2622-63-1|1-Methyl-2-phenyl-1H-benzo[d]imidazole| Ambeed

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Quality Control of [ 2622-63-1 ] Purity: 97% SDS Specification

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Product Details of [ 2622-63-1 ]

CAS No. :	2622-63-1
Formula :	C₁₄H₁₂N₂
M.W :	208.26
SMILES Code :	CN1C2=CC=CC=C2N=C1C3=CC=CC=C3
MDL No. :	MFCD00005764
InChI Key :	POSRBSJJCMKQNU-UHFFFAOYSA-N
Pubchem ID :	75807

Safety of [ 2622-63-1 ]

GHS Pictogram:
Signal Word:	Warning
Hazard Statements:	H317-H319
Precautionary Statements:	P280-P305+P351+P338

Computational Chemistry of [ 2622-63-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	16
Num. arom. heavy atoms	15
Fraction Csp3	0.07
Num. rotatable bonds	1
Num. H-bond acceptors	1.0
Num. H-bond donors	0.0
Molar Refractivity	66.43
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	17.82 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.3
Log P_o/w (XLOGP3)? XLOGP3: Atomistic and knowledge-based method calculated by XLOGP program, version 3.2.2, courtesy of CCBG, Shanghai Institute of Organic Chemistry	3.1
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	3.24
Log P_o/w (MLOGP)? MLOGP: Topological method implemented from Moriguchi I. et al. 1992 Chem. Pharm. Bull. Moriguchi I. et al. 1994 Chem. Pharm. Bull. Lipinski PA. et al. 2001 Adv. Drug. Deliv. Rev.	3.07
Log P_o/w (SILICOS-IT)? SILICOS-IT: Hybrid fragmental/topological method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	3.02
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.95

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-3.71
Solubility	0.0404 mg/ml ; 0.000194 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (Ali)? Ali: Topological method implemented from Ali J. et al. 2012 J. Chem. Inf. Model.	-3.14
Solubility	0.15 mg/ml ; 0.000721 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Soluble
Log S (SILICOS-IT)? SILICOS-IT: Fragmental method calculated by FILTER-IT program, version 1.0.2, courtesy of SILICOS-IT, http://www.silicos-it.com	-5.0
Solubility	0.0021 mg/ml ; 0.0000101 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	Moderately soluble

Pharmacokinetics

GI absorption? Gatrointestinal absorption: according to the white of the BOILED-Egg	High
BBB permeant? BBB permeation: according to the yolk of the BOILED-Egg	Yes
P-gp substrate? P-glycoprotein substrate: SVM model built on 1033 molecules (training set) and tested on 415 molecules (test set) 10-fold CV: ACC=0.72 / AUC=0.77 External: ACC=0.88 / AUC=0.94	Yes
CYP1A2 inhibitor? Cytochrome P450 1A2 inhibitor: SVM model built on 9145 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.83 / AUC=0.90 External: ACC=0.84 / AUC=0.91	Yes
CYP2C19 inhibitor? Cytochrome P450 2C19 inhibitor: SVM model built on 9272 molecules (training set) and tested on 3000 molecules (test set) 10-fold CV: ACC=0.80 / AUC=0.86 External: ACC=0.80 / AUC=0.87	Yes
CYP2C9 inhibitor? Cytochrome P450 2C9 inhibitor: SVM model built on 5940 molecules (training set) and tested on 2075 molecules (test set) 10-fold CV: ACC=0.78 / AUC=0.85 External: ACC=0.71 / AUC=0.81	No
CYP2D6 inhibitor? Cytochrome P450 2D6 inhibitor: SVM model built on 3664 molecules (training set) and tested on 1068 molecules (test set) 10-fold CV: ACC=0.79 / AUC=0.85 External: ACC=0.81 / AUC=0.87	Yes
CYP3A4 inhibitor? Cytochrome P450 3A4 inhibitor: SVM model built on 7518 molecules (training set) and tested on 2579 molecules (test set) 10-fold CV: ACC=0.77 / AUC=0.85 External: ACC=0.78 / AUC=0.86	Yes
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.37 cm/s

Druglikeness

Lipinski? Lipinski (Pfizer) filter: implemented from Lipinski CA. et al. 2001 Adv. Drug Deliv. Rev. MW ≤ 500 MLOGP ≤ 4.15 N or O ≤ 10 NH or OH ≤ 5	0.0
Ghose? Ghose filter: implemented from Ghose AK. et al. 1999 J. Comb. Chem. 160 ≤ MW ≤ 480 -0.4 ≤ WLOGP ≤ 5.6 40 ≤ MR ≤ 130 20 ≤ atoms ≤ 70	None
Veber? Veber (GSK) filter: implemented from Veber DF. et al. 2002 J. Med. Chem. Rotatable bonds ≤ 10 TPSA ≤ 140	0.0
Egan? Egan (Pharmacia) filter: implemented from Egan WJ. et al. 2000 J. Med. Chem. WLOGP ≤ 5.88 TPSA ≤ 131.6	0.0
Muegge? Muegge (Bayer) filter: implemented from Muegge I. et al. 2001 J. Med. Chem. 200 ≤ MW ≤ 600 -2 ≤ XLOGP ≤ 5 TPSA ≤ 150 Num. rings ≤ 7 Num. carbon > 4 Num. heteroatoms > 1 Num. rotatable bonds ≤ 15 H-bond acc. ≤ 10 H-bond don. ≤ 5	0.0
Bioavailability Score? Abbott Bioavailability Score: Probability of F > 10% in rat implemented from Martin YC. 2005 J. Med. Chem.	0.55

Medicinal Chemistry

PAINS? Pan Assay Interference Structures: implemented from Baell JB. & Holloway GA. 2010 J. Med. Chem.	0.0 alert
Brenk? Structural Alert: implemented from Brenk R. et al. 2008 ChemMedChem	0.0 alert: heavy_metal
Leadlikeness? Leadlikeness: implemented from Teague SJ. 1999 Angew. Chem. Int. Ed. 250 ≤ MW ≤ 350 XLOGP ≤ 3.5 Num. rotatable bonds ≤ 7	No; 1 violation:MW<1.0
Synthetic accessibility? Synthetic accessibility score: from 1 (very easy) to 10 (very difficult) based on 1024 fragmental contributions (FP2) modulated by size and complexity penaties, trained on 12'782'590 molecules and tested on 40 external molecules (r² = 0.94)	1.65

Application In Synthesis of [ 2622-63-1 ]

* All experimental methods are cited from the reference, please refer to the original source for details. We do not guarantee the accuracy of the content in the reference.

Downstream synthetic route of [ 2622-63-1 ]

[ 2622-63-1 ] Synthesis Path-Downstream 1~35

1
[ 25148-68-9 ]
[ 100-52-7 ]
[ 2622-63-1 ]

References: [1]Chemische Berichte,1942,vol. 75,p. 1936,1942.
[2]Journal of Organic Chemistry,2017,vol. 82,p. 3152 - 3158.

2
[ 64-17-5 ]
[ 100-52-7 ]
[ 4760-34-3 ]
[ 2622-63-1 ]

References: [1]Chemische Berichte,1892,vol. 25,p. 2826.

3
[ 2622-63-1 ]
[ 36016-40-7 ]
[ 59523-27-2 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

4
[ 3652-92-4 ]
[ 882-33-7 ]
[ 2622-63-1 ]
[ 100-68-5 ]
[ 108-98-5 ]
1,3-Dimethyl-2-phenylbenzenediazolium phenylthiolate [ No CAS ]

References: [1]Journal of Organic Chemistry,1992,vol. 57,p. 662 - 666.

5
[ 120914-33-2 ]
[ 6299-90-7 ]
[ 2622-63-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

6
[ 616-38-6 ]
[ 716-79-0 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
	With 1,8-diazabicyclo[5.4.0]undec-7-ene; In dichloromethane;	EXAMPLE 4 Preparation of 1-Methyl-2-Phenylbenzimidazole Using DBU To a mixture of 2-phenylbenzimidazole (1.02 g, 5.25 mmol) in DMC (10 mL), DBU (0.80 g, 5.25 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 6 hours. The solvent was evaporated under vacuum and the resulting oil was dissolved in methylene chloride (2 mL) and filtered through silica gel (2:1 EtOAc/hexane). The solvent was evaporated under vacuum to afford 1-methyl-2-phenylbenzimidazole as a solid. The yield of 1-methyl-2-phenylbenzimidazole as determined by HPLC analysis was 98percent conversion.
		EXAMPLE 5 Preparation of 1-methyl-2-phenylbenzimidazole Using Dabco.(TM). To a mixture of 2-phenylbenzimidazole (2.02 g, 10.4 mmol) in DMC (10 mL), Dabco.(TM). (1.17 g, 10.4 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 3 hours. The yield of 1-methyl-2-phenylbenzimidazole as determined by HPLC analysis was 99percent conversion.
	With dmap; In N,N-dimethyl-formamide;	EXAMPLE 6 Preparation of 1-Methyl-2-phenylbenzimidazole Using DMAP To a mixture of 2-phenylbenzimidazole (2.02 g, 10.4 mmol) in DMC (10 mL) and DMF (5 mL), DMAP (1.27 g, 10.4 mmol) was added and the resulting mixture was heated to reflux (90° C.) for 4 hours. The yield of 1-methyl-2-phenylbenzimidazole as determined by HPLC analysis was 99percent conversion.

References: [1]Organic Letters,2001,vol. 3,p. 4279 - 4281.
[2]Liebigs Annalen der Chemie,1987,p. 77 - 80.
[3]Patent: US2003/73848,2003,A1 .
[4]Patent: US2003/73848,2003,A1 .
[5]Patent: US2003/73848,2003,A1 .

7
[ 612-28-2 ]
[ 100-46-9 ]
[ 2622-63-1 ]
[ 716-79-0 ]

References: [1]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,1980,vol. 19,p. 655 - 658.

8
[ 53114-86-6 ]
[ 2622-63-1 ]

References: [1]Chemistry of Heterocyclic Compounds,1987,vol. 23,p. 1090 - 1094.
Khimiya Geterotsiklicheskikh Soedinenii,1987,p. 1360 - 1364.

9
p-(1-methylbenzimidazol-2-yl)phenyl(triphenyl)phosphonium bromide [ No CAS ]
[ 2622-63-1 ]
[ 2562-78-9 ]
[ 791-28-6 ]

References: [1]Phosphorus, Sulfur and Silicon and the Related Elements,1994,vol. 86,p. 259 - 262.
[2]Journal of the Chemical Society. Perkin transactions I,1995,p. 2789 - 2794.
[3]Journal of the Chemical Society. Perkin transactions I,1995,p. 2789 - 2794.

10
o-(1-methylbenzimidazol-2-yl)phenyl(triphenyl)phosphonium bromide [ No CAS ]
[ 2622-63-1 ]
[ 791-28-6 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1995,p. 2789 - 2794.
[2]Journal of the Chemical Society. Perkin transactions I,1995,p. 2789 - 2794.

11
1-ethoxycarbonyl-3-methyl-2-phenylbenzimidazolium methosulfate [ No CAS ]
[ 2622-63-1 ]

References: [1]Tetrahedron,1996,vol. 52,p. 6569 - 6580.

12
1-ethoxycarbonyl-3-methyl-2-phenylbenzimidazolium methosulfate [ No CAS ]
[ 2622-63-1 ]
[2-(Benzoyl-methyl-amino)-phenyl]-carbamic acid ethyl ester [ No CAS ]

References: [1]Tetrahedron,1996,vol. 52,p. 6569 - 6580.

13
[ 2622-63-1 ]
[ 74-88-4 ]
[ 3653-05-2 ]

Yield	Reaction Conditions	Operation in experiment
95%	In N,N-dimethyl-formamide; for 0.0833333h;Microwave irradiation;	General procedure: 2 mmols of 1-methyl-2-aryllbenzimidazole was placed ina 100 mL round bottom flask. After adding 2 mL of DMF into the flask, 3 mmols of alkylhalide was added onto the mixture dropwise under stirring. Attaching with a reflux condenser, the reaction system was placed in the CEM-Mars6 multimode microwave synthesis system and exposed to 120 W microwaves. The progress and termination of the reaction was monitored by TLC with a mixture of methanol and chloroform (1:9) as the eluent. After termination of the reaction, the heterogenous mixture obtained was cooled to room temperature and then poured into diethyl ether (30mL). The precipitate was collected by filtration. Diethylether threatment was repeated two times in order to remove solvent residue. The insoluble light brown/beige solids obtained by filtration was allowed to crystallize in water. Compounds 8-28 were synthesised from appropriate 1-methl-2-arylbenzimidazole derivatives and alkyl halides using the same procedure.
91%	In dichloromethane; at 30℃; for 17h;	Methylene chloride (20 mL) was added to 7 (3.00 g, 14.4 mmol) in a 50 mL round-bottom flask and stirred until fully dissolved. Iodomethane (2.7 mL, 43.4 mmol) was added and the mixture was stirred at 30 °C closed for 17 h. The solvent was evaporated at 45 °C using dynamic vacuum and diethyl ether was added. The solid was collected by vacuum filtration, washed with diethyl ether, and dried under vacuum at 40 °C, yielding HB (4.59 g, 91percent) as an off-white powder. 1H NMR (500 MHz, DMSO-d6, delta 8.15 (dd, J= 6.2, 3.1 Hz, 2H), 7.93 (d, J= 7.0 Hz, 2H), 7.88-7.73 (m, 5H), 3.91 (s, 6H). 13C NMR (125 MHz, DMSO-d6, delta: 150.29, 132.91, 131.68, 130.76, 129.42, 126.61,120.96, 113.39, 32.85. ESI-MS m/z calcd for C15H15N2+ [M+]: 223.123, found 223.124.

References: [1]Letters in drug design and discovery,2018,vol. 15,p. 621 - 633.
[2]Patent: WO2017/117678,2017,A1 .Location in patent: Page/Page column 40; 41.
[3]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 672 - 681.
[4]Angewandte Chemie - International Edition,2016,vol. 55,p. 4818 - 4821.
Angew. Chem.,2016,vol. 128,p. 4898 - 4902,5.

14
[ 716-79-0 ]
[ 74-88-4 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
85%		Powdered potassium hydroxide (2.24 g, 39.9 mmol) was added to a 250 mL round-bottom flask and vigorously stirred in DMSO (65 mL) for 30 min. A solution of 2- phenylbenzimidazole (4.11 g, 21.2 mmol) in DMSO (65 mL) was added to the basic DMSO solution and the mixture stirred for 45 min closed at room temperature. Iodomethane (1.4 mL, 22.5 mmol) was then added and the mixture stirred for 45 min. The mixture was then poured into a stirring solution of water (1.0 L) containing potassium hydroxide (5.0 g). Diethyl ether (300 mL) was then added and stirred until both layers were transparent. The organic layer was decanted and the same process was repeated with additional diethyl ether (2 x 200 mL). The combined organics were washed with water, brine, water, dried over magnesium sulfate, filtered, and evaporated at 44 °C under dynamic vacuum to yield 7 (3.74 g, 85percent) as a pale brown powder.1HNMR (500MHz, DMSO-d6, delta 7.86 (dd, J= 7.8, 1.7Hz, 2H), 7.69 (d, J= 7.9Hz,1H), 7.64-7.52 (m, 4H), 7.33-7.22 (m, 2H), 3.88 (s, 3H). 13C NMR (125 MHz, DMSOd 6, delta): 152.98, 142.47, 136.57, 130.15, 129.60, 129.28, 128.63, 122.32, 121.90, 118.98, 110.53, 31.64.
62%		Under an atmospheric nitrogen gas flow, sodium hydride in an amount of 12.8 mmol (containing 438 mg of 30 percent liquid paraffin) was placed into a three neck flask having a capacity of 100 milliliter, and adding n-pentane in an amount of 10 milliliter, the resultant solution was stirred at room temperature for 15 minutes. Subsequently, n-pentane was removed and then, after adding n-pentane again, the resultant solution was stirred. Repeating the above operation 4 times totally, the liquid paraffin was removed. Afterwards, the refined sodium hydride was vacume dried among the flask. Then, adding N,N-dimethylformamide in an amount of 15 milliliter and hpbi in an amount of 7.7 mmol (1.5 g), the resultant solution was stirred at a temperature of 35 °C for 1 hour and, further adding methyl iodide in an amount of 9.6 mmol (1.36 g), the resultant solution was further stirred at a temperature of 40 °C for 3 hours. After the resultant solution was cooled by leaving it standing, the solvent was removed by pressure reduction, and adding pure water, the resultant solution was stirred. Further, after adding dichloromethane, the resultant solution was divided by extraction. Gathering an organic layer, and after dehydration with the use of sodium sulfate, the solvent was concentrated by pressure reduction. A white precipitate generated by adding n-hexane was separated by filtration and 0.99 g of the aimed substance was obtained (yield: 62 percent).
49%	In acetone; at 20℃; for 6h;	The synthesis of 1-methyl-2-phenyl-1H-benzoimidazole (Mpb) is accomplished by referring to methods disclosed in Popov, 1. I., Chem. Heterocycl. Compd. (EN), 1996, 32, 6, p.672-681. The synthetic method is outlined in Scheme 1. To 20 mL acetone was added 2-phenyl-1H-benzoimidazole (1.94 g, 10 mmol), followed by the injection of iodomethane (1.42 mL, 12 mmol). The mixture was stirred at room temperature for 6 h, sodium hydroxide solution was then added, and the mixture reacted for an additional 5 min. The reaction mixture was extracted with dichloromethane. The organic layer was dried over magnesium sulfate and concentrated under reduced pressure. The residue was purified by column chromatography using n-hexanes/EA (v/v=80/20) as eluent. After the product was completely isolated, 1.03 mg (0.49 mmol) of the title compound was obtained (49percent yield). 1H NMR (CDCl3, delta): 3.87 (s, 3 H), 7.32-7.41 (m, 3 H), 7.51-7.56 (m, 3 H), 7.83-7.86 (m, 3 H).

8 g

With potassium tert-butylate; In tetrahydrofuran; at 20℃;

2-Phenyl-1H-benzo [d] imidazole (10 g, Tokyo Chemical Industry) was dissolved in dehydrated tetrahydrofuran (200 ml, Wako Pure Chemical Industries), potassium t-butoxide (6.07 g, Wako Junyaku), iodinated Methyl (3.85 ml, Wako Pure Chemical Industries, Ltd.) was added and the mixture was stirred overnight at room temperature. After the reaction, the reaction mixture was extracted with chloroform (Wako Pure Chemical Industries, Ltd.), washed twice with water, and the organic layer was recovered. The organic layer was dried with anhydrous sodium sulfate (Wako Pure Chemical Industries, Ltd.) and concentrated. The residue was purified by silica gel column chromatography to obtain 8 g of 1-methyl-2-phenyl-1H-benzo [d] imidazole.

References: [1]Journal of the American Chemical Society,2013,vol. 135,p. 3407 - 3410.
[2]Chemical Communications,2014,vol. 50,p. 14129 - 14132.
[3]Angewandte Chemie - International Edition,2016,vol. 55,p. 4818 - 4821.
Angew. Chem.,2016,vol. 128,p. 4898 - 4902,5.
[4]Patent: WO2017/117678,2017,A1 .Location in patent: Page/Page column 40; 41.
[5]Chemistry of Heterocyclic Compounds,1996,vol. 32,p. 672 - 681.
[6]Patent: EP1816134,2007,A1 .Location in patent: Page/Page column 28.
[7]Helvetica Chimica Acta,2006,vol. 89,p. 841 - 853.
[8]Patent: US2005/116626,2005,A1 .Location in patent: Page/Page column 11.
[9]Journal of Organometallic Chemistry,2012,vol. 702,p. 27 - 35.
[10]Chemical Communications,2017,vol. 53,p. 1041 - 1044.
[11]Patent: JP2018/135337,2018,A .Location in patent: Paragraph 0050; 0051.

15
[ 1632-83-3 ]
[ 108-86-1 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
88%	With copper(II) oxide; potassium carbonate; triphenylphosphine; In diethylene glycol dimethyl ether; at 160℃; for 24h;Reflux; Inert atmosphere; Sealed tube;	General procedure: 4.3 General procedure for CuO-catalyzed arylation and alkenylation of 1,3-azole (0012) Under argon, 0.5mmol of the bromobenzene or bromoalkene was added to the reaction mixture containing 0.25mmol of the benzoxazole, 0.5mmol K2CO3, 0.025mmol CuO, and 0.075mmol PPh3, followed by the addition of 2mL dry diglyme. The sealed reaction tube was stirred at 160°C for 5?24h. After cooling, the reaction mixture was centrifuged to remove solid and separated the organic phase. Then, organic phase was extracted and dried over anhydrous MgSO4, and concentrated under reduced pressure after filtered. The residue was purified by column chromatography on silica gel eluted to afford corresponding product.

References: [1]Tetrahedron,2014,vol. 70,p. 6120 - 6126.
[2]Heterocycles,2011,vol. 83,p. 1371 - 1376.
[3]Journal of the American Chemical Society,2008,vol. 130,p. 2493 - 2500.
[4]Journal of the American Chemical Society,2010,vol. 132,p. 3674 - 3675.
[5]Angewandte Chemie - International Edition,2006,vol. 45,p. 1589 - 1591.
[6]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 467 - 473.

16
[ 1632-83-3 ]
[ 591-50-4 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With 10 molpercent nickel based 2,5-dihydroxyterephthalic acid metal organic framework-74; In diethylene glycol dimethyl ether; at 160℃; for 18h;Sealed tube;	General procedure: In a typical experiment, a predetermined amount of Ni-MOF-74 was added to the 8 mL vial containing a mixture of iodobenzene (0.1030 g, 0.5 mmol), benzothiazole (0.1379 g, 1.0 mmol), Li2CO3 or KCl (1.0 mmol), and diphenyl ether (0.085 g, 0.5 mmol) as standard. 1-Methoxy-2-(2-methoxyethoxy)ethane (diglyme) (1 mL) was added and vial was tightly capped. Reaction mixture was heated at 160°C for 24 h. The catalyst loading was based on the molar ratio of nickel/iodobenzene. The reaction yield was monitored by withdrawing aliquots from the reaction mixture at different time intervals, diluting with ethylacetate (2 mL), quenching with an aqueous KOH solution (1percent, 1 mL), and then drying over anhydrous Na2SO4 before analyzing by GC with reference to diphenyl ether (internal equation with pure product), and further confirming product identity by GC?MS and NMR. To investigatethe recycle ability of Ni-MOF-74, the catalyst was filtered from the reaction mixture after the experiment, washed with ethylacetate, water, THF, and dried at 140°C under vacuum in 8 h. For the leaching test, a catalytic reaction was stopped after 12 h, analyzed by GC, and filtered to remove the solid catalyst. The reaction solution was then stirred for a further 12 h. Reaction progress, if any, was monitored by GC as previously described.
67%	With (1-(2-(tert-butylamino)ethyl)-3-mesityl-2,3-dihydro-1H-imidazol-2-yl)copper(I) iodide; lithium tert-butoxide; In N,N-dimethyl-formamide; at 140℃; for 8h;Glovebox;	General procedure: The product 12a is a representative reaction. To a vial (5 mL) containing caffeine (0.5 mmol), iodobenzene (1.0 mmol), catalyst 3e (0.05 mmol), and LiOtBu (1.0 mmol) was added DMF (1.0 mL) solvent under a glovebox atmosphere. After the substances were completely dissolved, the vial was screw-capped, taken outside the glovebox and heated at 140 °C for 8 h. The resulting mixture was filtered through Celite and washed with dichloromethane. The filtrate solution was concentrated in vacuo to afford the crude product, which was further purified by column chromatography using hexane/ethyl acetate as eluent to furnish 12a in 80percent yield.
46%	With potassium phosphate; Cu2(4,4?-biphenyldicarboxylate)2(4,4?-bipyridine); In Hexadecane; N,N-dimethyl-formamide; at 120℃; for 3h;Green chemistry;	General procedure: In a typical experiment, a pre-determined amount of Cu2(BPDC)2(BPY) was added to theflask containing a solution of iodobenzene (0.112 mL, 1 mmol),benzoxazole (0.238 g, 2 mmol), K3PO4(0.532 g, 2 mmol) and n-hexadecane (0.1 mL) as internal standard in DMF (4 mL). Thecatalyst concentration was calculated based on the molar ratio ofcopper/iodobenzene. The reaction mixture was stirred at 100Cunder an argon atmosphere for 180 min. The reaction conver-sion was monitored by withdrawing aliquots from the reactionmixture at different time intervals, quenching with an aqueousNaOH solution (5percent, 1 mL), drying over anhydrous Na2SO4, analyz-ing by GC with reference to n-hexadecane, and further confirmingproduct identity by GC?MS. To investigate the recyclability ofCu2(BPDC)2(BPY), the catalyst was filtered from the reaction mix-ture after the experiment, washed with copious amounts of DMF,dried under air at room temperature for 1 h, and reused if neces-sary. For the leaching test, a catalytic reaction was stopped after30 min, analyzed by GC, and filtered to remove the solid catalyst.The reaction solution was then stirred for a further 150 min. Reac-tion progress, if any, was monitored by GC as previously described.

References: [1]Angewandte Chemie - International Edition,2007,vol. 46,p. 7996 - 8000.
[2]Journal of Molecular Catalysis A: Chemical,2017,vol. 426,p. 141 - 149.
[3]Journal of Organic Chemistry,2011,vol. 76,p. 4741 - 4745.
[4]Journal of the American Chemical Society,2007,vol. 129,p. 12404 - 12405.
[5]Bulletin of the Chemical Society of Japan,1998,vol. 71,p. 467 - 473.
[6]Tetrahedron Letters,2008,vol. 49,p. 1598 - 1600.
[7]Advanced Synthesis and Catalysis,2017,vol. 359,p. 772 - 778.
[8]Journal of Organometallic Chemistry,2014,vol. 761,p. 64 - 73.
[9]Organic Letters,2004,vol. 6,p. 35 - 38.
[10]Journal of Molecular Catalysis A: Chemical,2014,vol. 391,p. 74 - 82.
[11]Organic Letters,2009,vol. 11,p. 1733 - 1736.
[12]Chemistry - A European Journal,2011,vol. 17,p. 10113 - 10122.
[13]RSC Advances,2014,vol. 4,p. 52307 - 52315.

17
N-methyl-N'-(2,2,2-trifluoro-1-phenyl-ethylidene)-benzene-1,2-diamine [ No CAS ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 4119 - 4122.

Yield	Reaction Conditions	Operation in experiment
90%	With potassium iodide; In N,N-dimethyl-formamide; at 80℃;Molecular sieve;	General procedure: Phenylenediamine (1.0 mmol),Benzaldehyde (1.1 mmol) and KI (166 mg, 1.0 mmol) were dissolved in 10 ml of DMF,The inlet of the reaction vessel was opened to form an atmosphere to be exposed to the air, and 4 A molricular sieve was added thereto to provide an anhydrous condition, followed by stirring at 80 °C.The reaction was terminated by checking the amount of phenylenediamine consumed. After cooling to room temperature, the solvent was distilled off under reduced pressure, and the reaction mixture was separated by column chromatography to obtain 176 mg of the target compound of the formula (4). Yield 91percent

20
N-(2-bromo-phenyl)-N'-methyl-benzamidine [ No CAS ]
[ 2622-63-1 ]

References: [1]Journal of Organic Chemistry,2003,vol. 68,p. 6814 - 6816.
[2]Tetrahedron Letters,2002,vol. 43,p. 1893 - 1895.

21
[ 120-51-4 ]
[ 4760-34-3 ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 313 - 316.

22
[ 4760-34-3 ]
hydroxymethyl JandaJel^TM resin-bound benzoyl ester [ No CAS ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,2004,vol. 45,p. 313 - 316.

23
[ 100-52-7 ]
[ 4760-34-3 ]
[ 2622-63-1 ]

Yield	Reaction Conditions	Operation in experiment
97%	With sodium metabisulfite; In N,N-dimethyl-formamide;Reflux;	8.4 g of compound c1, 7 g of benzaldehyde, 13gSodium metabisulfite,200mL dimethylformamide was added to the reaction flask Medium, reflux overnight. After the reaction is finished, cool to room temperature.Pour the reaction solution into 500 mL of ice water with stirring.Solid precipitated, suction filtered, and washed with ethanol, petroleum ether,Drying gave a solid, Compound d1 (11.3 g, yield 97percent).
94%	With Ag2CO3/celite; In ethanol; at 70℃; for 3h;	General procedure: To a mixture of 1,2-phenylenediamines (1.0 mmol) andaldehydes (1.1 mmol) in ethanol, 25 mol percent of Ag2CO3/Celite (3 mL) was added. The resulting mixture was stirredat 70 °C for 3 h. After this time, the reaction mixture wasdiluted with ethanol (50 mL) and the catalyst was separatedby filtration. Water was then added to the organic layer, andthe products were filtered and washed with water. All of theproducts are known compounds and characterized easily bycomparison with melting point, IR, [1?6] H NMR spectraldata reported in literature.
90%	In water; N,N-dimethyl-formamide; at 80℃;	General procedure: An ortho-phenylenediamine derivative 3 (1.0 mmol; 1.0 equiv) and an aldehyde 4 (1.0 mmol; 1.0 equiv) were dissolved in wet DMF (DMF 9.0 mL, H2O 1.0 mL). The resulting reaction mixture was stirred at 80°C in an open flask, and the reaction progress was monitored by TLC. On the complete consumption of 3, the reaction mixture was cooled to room temperature and concentrated under reduced pressure. The crude product obtained was purified by column chromatography on silica gel to afford the corresponding benzimidazole 5.

References: [1]Patent: CN108774266,2018,A .Location in patent: Paragraph 0070; 0071; 0075.
[2]Journal of the Iranian Chemical Society,2015,vol. 12,p. 1281 - 1285.
[3]Tetrahedron,2015,vol. 71,p. 532 - 538.
[4]Organic and Biomolecular Chemistry,2013,vol. 11,p. 3776 - 3780.
[5]Monatshefte fur Chemie,2009,vol. 140,p. 375 - 380.
[6]Tetrahedron Letters,2007,vol. 48,p. 5239 - 5242.
[7]Synlett,2004,p. 1832 - 1834.
[8]Synthetic Communications,2011,vol. 41,p. 2304 - 2308.

24
[ 4760-34-3 ]
[ 100-51-6 ]
[ 2622-63-1 ]

References: [1]Synlett,2004,p. 1628 - 1630.

25
[ 65-85-0 ]
[ 4760-34-3 ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,2006,vol. 47,p. 2883 - 2886.

26
C₁₄H₁₄N₂O [ No CAS ]
[ 2622-63-1 ]

References: [1]Organic Letters,2007,vol. 9,p. 4749 - 4751.

27
[ 95-54-5 ]
pyridine-dicarboxylic acid-(2.3)-2-ethyl ester [ No CAS ]
[ 2622-63-1 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 841 - 853.

28
[ 65-85-0 ]
inactivated menthene [ No CAS ]
[ 2622-63-1 ]

References: [1]Helvetica Chimica Acta,2006,vol. 89,p. 841 - 853.

29
[ 88070-48-8 ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1893 - 1895.

30
[ 615-36-1 ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,2002,vol. 43,p. 1893 - 1895.

31
[ 4760-34-3 ]
[ 2622-63-1 ]

References: [1]Tetrahedron Letters,1999,vol. 40,p. 4119 - 4122.

32
[ 98-88-4 ]
O⁵-benzoyl-O¹,O²-isopropyliden-β-D-arabinofuranose [ No CAS ]
[ 2622-63-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

33
[ 120914-36-5 ]
[ 2622-63-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

34
Benzoic acid N'-(2-amino-phenyl)-N,N'-dimethyl-hydrazide [ No CAS ]
[ 2622-63-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

35
[ 120914-37-6 ]
[ 2622-63-1 ]

References: [1]Journal of the Chemical Society. Perkin transactions I,1988,p. 3381 - 3386.

Historical Records

Technical Information

• Reactions of Benzene and Substituted Benzenes

Related Functional Groups of
[ 2622-63-1 ]

Aryls

A192102 [716-79-0]

2-Phenyl-1H-benzo[d]imidazole

Similarity: 0.96

A240163 [2963-77-1]

4-(1H-Benzo[d]imidazol-2-yl)aniline

Similarity: 0.96

A155013 [13676-49-8]

2-(3-Aminophenyl)-1H-benzo[d]imidazol-6-amine

Similarity: 0.93

A306280 [760212-58-6]

1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole

Similarity: 0.87

A207724 [621-72-7]

2-Benzyl-1H-benzo[d]imidazole

Similarity: 0.85

Related Parent Nucleus of
[ 2622-63-1 ]

Benzimidazoles

A192102 [716-79-0]

2-Phenyl-1H-benzo[d]imidazole

Similarity: 0.96

A240163 [2963-77-1]

4-(1H-Benzo[d]imidazol-2-yl)aniline

Similarity: 0.96

A155013 [13676-49-8]

2-(3-Aminophenyl)-1H-benzo[d]imidazol-6-amine

Similarity: 0.93

A306280 [760212-58-6]

1-(4-Bromophenyl)-2-phenyl-1H-benzo[d]imidazole

Similarity: 0.87

A207724 [621-72-7]

2-Benzyl-1H-benzo[d]imidazole

Similarity: 0.85

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CAS No.: 2622-63-1

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