41014-43-1|2-(Chloromethyl)benzo[d]oxazole| Ambeed

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Structure of 41014-43-1

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Quality Control of [ 41014-43-1 ] Purity: 95% SDS Specification

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Product Details of [ 41014-43-1 ]

CAS No. :	41014-43-1
Formula :	C₈H₆ClNO
M.W :	167.59
SMILES Code :	ClCC1=NC2=C(O1)C=CC=C2
MDL No. :	MFCD05664964
InChI Key :	ANRDUCQCZKLSGF-UHFFFAOYSA-N
Pubchem ID :	2061989

Safety of [ 41014-43-1 ]

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H302-H314
Precautionary Statements:	P260-P264-P270-P280-P301+P330+P331-P303+P361+P353-P304+P340-P305+P351+P338-P310-P363-P405-P501
Class:	8
UN#:	3265
Packing Group:	Ⅱ

Computational Chemistry of [ 41014-43-1 ] Show Less

Physicochemical Properties

Num. heavy atoms	11
Num. arom. heavy atoms	9
Fraction Csp3	0.12
Num. rotatable bonds	1
Num. H-bond acceptors	2.0
Num. H-bond donors	0.0
Molar Refractivity	43.77
TPSA ? Topological Polar Surface Area: Calculated from Ertl P. et al. 2000 J. Med. Chem.	26.03 Å²

Lipophilicity

Log P_o/w (iLOGP)? iLOGP: in-house physics-based method implemented from Daina A et al. 2014 J. Chem. Inf. Model.	2.07
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	2.43
Log P_o/w (WLOGP)? WLOGP: Atomistic method implemented from Wildman SA and Crippen GM. 1999 J. Chem. Inf. Model.	2.41
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.	1.63
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	2.85
Consensus Log P_o/w? Consensus Log P_o/w: Average of all five predictions	2.28

Water Solubility

Log S (ESOL):? ESOL: Topological method implemented from Delaney JS. 2004 J. Chem. Inf. Model.	-2.95
Solubility	0.188 mg/ml ; 0.00112 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.	-2.62
Solubility	0.403 mg/ml ; 0.0024 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	-3.93
Solubility	0.0198 mg/ml ; 0.000118 mol/l
Class? Solubility class: Log S scale Insoluble < -10 < Poorly < -6 < Moderately < -4 < Soluble < -2 Very < 0 < Highly	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	No
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	No
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	No
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	No
Log Kp (skin permeation)? Skin permeation: QSPR model implemented from Potts RO and Guy RH. 1992 Pharm. Res.	-5.6 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	1.0
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	1.0 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)	2.38

Application In Synthesis of [ 41014-43-1 ]

* 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 [ 41014-43-1 ]

[ 41014-43-1 ] Synthesis Path-Downstream 1~35

1
[ 41014-43-1 ]
[ 58287-50-6 ]
2-[2-(4,5-dihydro-1<i>H</i>-imidazol-2-yl)-4-nitro-phenylsulfanylmethyl]-benzooxazole [ No CAS ]

References: [1]Justus Liebigs Annalen der Chemie,1975,p. 1994 - 2005.

2
[ 41014-43-1 ]
[ 56313-90-7 ]

References: [1]Synthesis,1979,p. 102 - 103.

3
[ 36743-66-5 ]
[ 95-55-6 ]
[ 41014-43-1 ]

Yield	Reaction Conditions	Operation in experiment
95%	In dichloromethane; at 0 - 20℃;	B. To a stirred suspension of 2-aminophenol (365 mg, 3.35 mmol) in dichloromethane (7 mL) at 00C was added compound ethyl 2-chloroacetimidate hydrochloride (798 mg, 5.05 mmol) portion-wise. After 1 hour 25 min. at 00C, the mixture was stirred at ambient temperature overnight. The mixture was filtered through Celite and the filtrate was concentrated. The residue was purified by column (hexanes/EtOAc, 7/3) to afford 2-(chloromethyl)benzoxazole as a pale oil (533 mg, 95%).
86.5%	With acetic acid; In dichloromethane; at 0 - 20℃; for 1.41667h;	To a solution of 2-aminophenol (3.76 g,34.5 mmol) in methylene chloride at 0 C was added ethyl chloroacetimidate hydrochloride (7.98 g,50.5 mmol). After 85 min, the reaction mixture was allowed to warm to room temperature, while beingstirred overnight. The mixture was filtered over diatomite and concentrated to oil under reducedpressure. The resulting residue was purified by column chromatography on silica gel (petroleumether/acetone, 10:1 v:v) to obtain compound 3 as a white solid (5.00 g, 86.5%). m.p., 152-154 C;MS (+ESI) m/z 168.05 [M + H]+
75%	at 0℃; for 6h;	General procedure: General Method B: To the solution of substituted 2-aminophenol (1.0 equiv.) or substituted benzene-1, 2-diamine(1.0 equiv.) in DCM (or CH3OH), Int 1 (1.5 equiv.) was added and stirred at 0C overnight. The mixture was filteredwith celite. The filtrate was concentrated, purified by silica gel chromatography (EtOAc:hexane = 1:1) to afford thedesired products.

3.99 g (65%)	In ethanol; dichloromethane;	Step 1) Preparation of 2-(Chloromethyl)benzoxazole A mixture of o-aminophenol (4.00 g, 36.6 mmol) and ethyl chloroacetimidate hydrochloride (8.68 g, 54.98 mmol) in ethanol (55 mL) was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and vacuum filtered. The filtrate was concentrated in vacuo, diluted with dichloromethane and filtered again. The methylene chloride filtrate was dried (MgSO4) and concentrated to afford 3.99 g (65%) of product as a brown oil which was used directly in the next step. 1 H NMR (CDCl3): delta7.73 (m, 1H, ArH), 7.56 (m, 1H, ArH), 7.38 (m, 2H, ArH), 4.76 (s, 2H, CH2 Cl).
3.99 g (65%)	In ethanol; dichloromethane;	Step 1) Preparation of 2-(Chloromethyl)benzoxazole A mixture of o-aminophenol (4.00 g, 36.6 mmol) and ethyl chloroacetimidate hydrochloride (8.68 g, 54.98 mmol) in ethanol (55 mL) was heated at reflux for 18 hours. The reaction mixture was cooled to room temperature and vacuum filtered. The filtrate was concentrated in vacuo, diluted with methylene chloride and filtered again. The methylene chloride filtrate was dried (MgSO4) and concentrated to afford 3.99 g (65%) of product as a brown oil which was used directly in the next step. 1 H NMR (CDCl3): delta7.73 (m, 1H, ArH), 7.56 (m, 1H, ArH), 7.38 (m, 2H, ArH), 4.76 (s, 2H, CH2 Cl).

References: [1]European Journal of Medicinal Chemistry,2011,vol. 46,p. 1706 - 1712.
[2]Patent: WO2008/110793,2008,A1 .Location in patent: Page/Page column 103-104.
[3]Molecules,2018,vol. 23.
[4]Journal of Medicinal Chemistry,2012,vol. 55,p. 3066 - 3075.
[5]Bioorganic and Medicinal Chemistry,2019,vol. 27,p. 3089 - 3096.
[6]Synthesis,1979,p. 102 - 103.
[7]Patent: US5084463,1992,A .
[8]Patent: US5104892,1992,A .
[9]Inorganic Chemistry,2018,vol. 57,p. 11240 - 11251.

4
[ 123-75-1 ]
[ 41014-43-1 ]
[ 90298-68-3 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

5
[ 110-91-8 ]
[ 41014-43-1 ]
[ 90298-67-2 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

6
[ 41014-43-1 ]
[ 554-84-7 ]
[ 105785-68-0 ]

References: [1]Journal of medicinal chemistry,1987,vol. 30,p. 400 - 405.

7
[ 41014-43-1 ]
[ 135397-32-9 ]
[ 135525-70-1 ]

Yield	Reaction Conditions	Operation in experiment
	With triethylamine; In acetonitrile;	EXAMPLE 2 3-[(2-Benzoxazolylmethyl)amino]-5-ethyl-6-methyl-2-(1H)-pyridinone A solution of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (152 mg,1.0 mmol), <strong>[41014-43-1]2-chloromethyl-1,3-benzoxazole</strong> (1.07 mmol) and triethylamine (0.14 mL, 1.0 mmol) in acetonitrile (10 mmL) was stirred at reflux for 24 hrs. After concentrating under reduced pressure,the residue was flash chromatographed over silica gel. Elution with 5% MeOH- 95% CHCl3 gave 132 mg of product which was recrystallized from EtOH-water to give 95 mg of analytically pure product, mp 202-203C, with initial melting at 179 followed by resolidification. Anal. Calcd for
	With triethylamine; In acetonitrile;	EXAMPLE 2 3-[(2-Benzoxazolylmethyl)amino]-5-ethyl-6-methyl-2-(1H)-pyridinone A solution of 3-amino-5-ethyl-6-methyl-2-(1H)-pyridinone (152 mg,1.0 mmol), <strong>[41014-43-1]2-chloromethyl-1,3-benzoxazole</strong> (1.07 mmol) and triethylamine (0.14 mL, 1.0 mmol) in acetonitrile (10 mmL) was stirred at reflux for 24 hrs. After concentrating under reduced pressure,the residue was flash chromatographed over silica gel. Elution with 5% MeOH- 95% CHCl3 gave 132 mg of product which was recrystallized from EtOH-water to give 95 mg of analytically pure product, mp 202-203C, with initial melting at 179 followed by resolidification, Anal. Calcd for C16H17N3O2:

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3792 - 3802.
[2]Patent: EP462808,1991,A2 .
[3]Patent: EP484071,1992,A2 .

8
[ 41014-43-1 ]
[ 74772-78-4 ]
[ 107324-89-0 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 2617 - 2626.

9
[ 41014-43-1 ]
[ 139549-37-4 ]
[ 139548-38-2 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3792 - 3802.

10
[ 41014-43-1 ]
[ 139394-26-6 ]
[ 139394-27-7 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3792 - 3802.

11
[ 41014-43-1 ]
[ 143708-30-9 ]
[ 139394-28-8 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3792 - 3802.

12
[ 41014-43-1 ]
[ 143708-31-0 ]
[ 143708-18-3 ]

References: [1]Journal of Medicinal Chemistry,1992,vol. 35,p. 3792 - 3802.

13
[ 41014-43-1 ]
[ 139394-02-8 ]
[ 139394-03-9 ]

Yield	Reaction Conditions	Operation in experiment
46 mg (32%)	In N-methyl-acetamide; mineral oil;	Step E Preparation of 3-[(benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine A quantity of 60% sodium hydride in mineral oil (24 mg, 0.6 mmol) was added to a solution of 2-methoxy-3-hydroxy-5-ethyl-6-methylpyridine (77 mg, 0.46 mmol) in dry dimethylformamide (2 mL). After gas evolution ceased, 2-(chloromethyl) benzoxazole (100 mg, 0.6 mmol) was added and the reaction mixture warmed at 60 C. for one hour. The reaction was then cooled, diluted with diethyl ether, the ether extract washed with water, dried (Na2 SO4), filtered and evaporated to give 151 mg of crude mixture. This mixture was flash chromatographed on silica gel, eluding with 0.5% methanol/chloroform. Combined appropriate fractions gave 46 mg (32%) of oily product.
46 mg (32%)	In N-methyl-acetamide; mineral oil;	Step E : Preparation of 3-[(benzoxazol-2-yl)methoxy]-2-methoxy-5-ethyl-6-methylpyridine A quantity of 60% sodium hydride in mineral oil (24 mg, 0.6 mmol) was added to a solution of 2-methoxy-3-hydroxy-5-ethyl-6-methylpyridine (77 mg, 0.46 mmol) in dry dimethylformamide (2 mL). After gas evolution ceased, 2-(chloromethyl) benzoxazole (100 mg, 0.6 mmol) was added and the reaction mixture warmed at 60C for one hour. The reaction was then cooled, diluted with diethyl ether, the ether extract washed with water, dried (Na2SO4), filtered and evaporated to give 151 mg of crude mixture. This mixture was flash chromatographed on silica gel, eluding with 0.5% methanol/chloroform. Combined appropriate fractions gave 46 mg (32%) of oily product.

References: [1]Journal of Medicinal Chemistry,1993,vol. 36,p. 953 - 966.
[2]Patent: US5308854,1994,A .
[3]Patent: EP462808,1991,A2 .

14
[ 41014-43-1 ]
[ 83402-51-1 ]
[ 83397-10-8 ]

References: [1]Zeitschrift fur Naturforschung, Teil B: Anorganische Chemie, Organische Chemie,1982,vol. 37,p. 902 - 906.

15
[ 41014-43-1 ]
[ 101626-19-1 ]
[ 101626-22-6 ]

References: [1]Journal of medicinal chemistry,1987,vol. 30,p. 400 - 405.

16
[ 41014-43-1 ]
[ 100-44-7 ]
[ 125983-29-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

17
[ 41014-43-1 ]
[ 124-40-3 ]
[ 90298-69-4 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

18
[ 41014-43-1 ]
[ 121-44-8 ]
Benzooxazole-2-carbothioic acid diethylamide [ No CAS ]

References: [1]Zeitschrift fur Chemie,1988,vol. 28,p. 233 - 237.

19
[ 70737-12-1 ]
[ 95-55-6 ]
[ 41014-43-1 ]

References: [1]Journal of medicinal chemistry,1987,vol. 30,p. 400 - 405.

20
[ 41014-43-1 ]
[ 74-88-4 ]
[ 90298-66-1 ]

References: [1]Journal fur praktische Chemie (Leipzig 1954),1989,vol. 331,p. 243 - 262.

21
[ 10147-68-9 ]
[ 41014-43-1 ]

References: [1]Heterocycles,1995,vol. 41,p. 477 - 486.
[2]Journal of Fluorine Chemistry,2001,vol. 109,p. 39 - 48.
[3]Journal of Fluorine Chemistry,2000,vol. 102,p. 369 - 376.

22
[ 41014-43-1 ]
[ 122-52-1 ]
[ 18853-71-9 ]

References: [1]Heterocycles,1995,vol. 41,p. 477 - 486.

23
[ 79-04-9 ]
[ 95-55-6 ]
[ 41014-43-1 ]

Yield	Reaction Conditions	Operation in experiment
90.2%		In a solution of 2-aminophenol (0.50 g, 4.6 mmol) dissolved inchlorobenzene (5 mL), 2-chloroacetyl chloride (0.52 g, 4.6 mmol) and pyridine (0.02 mL) were added.The mixture was stirred at room temperature for 2 h; then p-toluene sulfonic acid (0.08 g, 0.46 mmol)was added. The mixture was heated at reflux for 8 h and then cooled to room temperature. The solventwas removed under reduced pressure, and the resulting residue was dissolved in ethyl acetate (30 mL).The solution was washed with water and brine, dried over Na2SO4, and concentrated in vacuo.The residue was puried by chromatography on silica gel (petroleum ether:ethyl acetate = 10:1) to give13g (0.70 g, 90.2%) as a yellow oil.
85%	With triethylamine; In 5,5-dimethyl-1,3-cyclohexadiene; at 20 - 145℃;Inert atmosphere;	This compound was synthesized according to the previously described procedure.5 To a solution of 2-aminophenol (0.50 g, 4.58 mmol, 1.0 equiv.) in xylene (20 mL), chloroacetyl chloride (0.56 mL, 6.87 mmol, 1.5 equiv.) was added under argon, followed by drop-wise addition of Et3N (0.70 mL, 5.04 mmol, 1.1 equiv.). The reaction mixture was initially stirred for 2 h at room temperature and then overnight at 145 C. A saturated aqueous solution of NH4Cl (50 mL) was added to the reaction mixture, and the biphasic system was transferred to a separating funnel. The mixture was extracted with EtOAc (3× 20 mL), and the combined organic phases were washed with saturated brine solution (50 mL), dried over Na2SO4, and evaporated under reduced pressure. The crude product was purified by short flash column chromatography using EtOAc/n-hex = 1/4 as eluent, to obtain 0.65 g of the compound. Yield: 85%; transparent yellow oil (lit.5 colorless oil); 1H NMR (400 MHz, CDCl3): delta 4.76 (s, 2H,CH2), 7.35-7.42 (m, 2H, 2 × Ar-H), 7.55-7.57 (m, 1H, Ar-H), 7.74-7.76 (m, 1H, Ar-H).
	With triethylamine; In xylenes; at 20 - 145℃;Inert atmosphere;	Under argon, chloroacetyl chloride (122 muL, 1.5 mmol) was added to a solution of 2-aminophenol (111 mg, 1 mmol) in xylenes (4 mL). Triethylamine (153 muL, 1.1 mmol) was next added dropwise. The resulting mixture was stirred for 2 hours at room temperature then at 145C overnight. An aqueous solution of ammonium chloride was added, and the mixture was extracted with ethyl acetate. The combined organic extracts were washed with brine, then dried over sodium sulfate, filtered and evaporated to give crude 2-(chloromethyl)-1,3-benzoxazole. The latter compound was placed in a screwed-cap tube, and dissolved in THF (0.5 mL). An aqueous ammonium hydroxide solution (33%, 4 mL) was added. The reaction mixture was stirred 30 minutes at room temperature then 22 hours at 60C. Ethyl acetate was added and ammonia was evaporated. The aqueous layer was acidified to pH = I with cold 1N aqueous hydrochloric acid. Extraction with diethyl ether and ethyl acetate gave organic extracts which were discarded.. The aqueous layer was basified with aqueous sodium hydroxide to pH = 10, then extracted with diethyl ether and ethyl acetate. Combined organic extracts were dried over sodium sulfate, filtered and evaporated to give crude 1,3-benzoxazol-2-ylmethylamine (19.4 mg, 13%) as a brown solid. ESI-MS m/z 149 (M+H)+.

		General procedure: The synthetic routes for compounds 1-3 are outlined in Scheme 3, and the detailed procedures are presented as follows: (a) To a solution of 2-aminophenol (16.35g, 150mmol) and chloroacetyl chloride (16.95g, 150mmol) in dry chlorobenzene (200mL) is added pyridine (0.5ml). The solution is stirred at ambient temperature for 2h. To above solution is added p-toluenesulfonic acid (2.58g, 15mmol), the solution is refluxed till no water is discharged. After cooling to room temperature, the solution is washed with water (100mL×3) and a saturated solution of NaCl (50mL), respectively. The organic solution is collected and dried over Na2SO4, after evaporation of the solvent, the crude 2-(chloromethyl)benzoxazole (yellow oil, 23.1g, 93% yield) is obtained for next step without purification. (b) To a solution of 2-(chloromethyl)benzoxazole (23.1g, 139.5mmol) and tetrabutylammonium bromide (4.49g, 13.95mmol) in dichloromethane (150ml) is added Na2S·9H2O (40.2g, 167.4mmol) in H2O (100ml), the mixture solution is stirred at ambient temperature for 4h until the starting material disappeared (TLC detection). The mixture solution is washed with water (100ml×3), the washed organic solution is then dried over Na2SO4, after evaporation of the solvent, the crude bis(benzoxazol-2-ylmethyl) sulfane (brown oil, 33.8g, 82% yield) is obtained for next step reaction without purification. (c) Sodium (1.15g, 50mmol) is added to anhydrous MeOH, the solution is stirred for 1hat ambient temperature. To above solution is added dropwise bis(benzoxazol-2-ylmethyl)sulfane (2.98g, 10mmol) and diethyl oxalate (1.46g, 10mmol) in dry DMF (20ml). The mixture solution is refluxed for 6h until no starting material is detected (TLC detection). After cooled to room temperature, the solution is acidified with HCl (12N, 50ml) till pH=3, the solid is filtered off and washed successively with EtOH (30ml), saturation NaHCO3 (30ml) and H2O (30ml). After dried in vacuo, the target compound 1 is obtained (yellow solid, 2.45g).
	With pyridine; toluene-4-sulfonic acid; In chlorobenzene; at 20℃; for 8h;Reflux;	The 2 - aminophenol (1.635 g), chloroacetyl chloride 1.2 ml, pyridine 0.5 ml, 20 ml chlorobenzene by adding 50 ml round bottom flask, stir at room temperature 2 h, to join the toluene sulfonic acid 0.258 g, reflux 6 h, TCL [...] monitoring, after the reaction, evaporation chlorobenzene, adding 100 ml water, extracted with ethyl acetate, 20 m1 * 3, water-free magnesium sulfate for steaming and after drying. The product is used DCM column, to obtain yellow oily liquid is the product.

References: [1]Molecules,2017,vol. 22.
[2]Bioorganic and Medicinal Chemistry,2015,vol. 23,p. 4442 - 4452.
[3]Recueil des Travaux Chimiques des Pays-Bas,1996,vol. 115,p. 337 - 338.
[4]Patent: EP2141164,2010,A1 .Location in patent: Page/Page column 38-39.
[5]Dalton Transactions,2008,p. 5715 - 5729.
[6]Chemical and Pharmaceutical Bulletin,2012,vol. 60,p. 449 - 458.
[7]Chinese Journal of Chemistry,2012,vol. 30,p. 1886 - 1892.
[8]Archiv der Pharmazie,2012,vol. 345,p. 745 - 752.
[9]Indian Journal of Chemistry - Section B Organic and Medicinal Chemistry,2013,vol. 52,p. 665 - 670.
[10]Dyes and Pigments,2016,vol. 129,p. 186 - 190.
[11]Journal of Heterocyclic Chemistry,2018,vol. 55,p. 1024 - 1032.
[12]Patent: CN109574949,2019,A .Location in patent: Paragraph 0062-0065.

24
[ 29804-89-5 ]
[ 95-55-6 ]
[ 41014-43-1 ]

References: [1]Recueil des Travaux Chimiques des Pays-Bas,1996,vol. 115,p. 337 - 338.

25
[ 98-01-1 ]
[ 41014-43-1 ]
[ 144154-59-6 ]

References: [1]Organic Preparations and Procedures International,1992,vol. 24,p. 520 - 522.

26
[ 41014-43-1 ]
[ 38788-38-4 ]
2-Benzoxazolylmethyldibutyltelluronium chloride [ No CAS ]

References: [1]Organic Preparations and Procedures International,1992,vol. 24,p. 520 - 522.

27
[ 41014-43-1 ]
[ 104-87-0 ]
[ 71907-25-0 ]

References: [1]Organic Preparations and Procedures International,1992,vol. 24,p. 520 - 522.

28
[ 41014-43-1 ]
[ 555-16-8 ]
[ 3271-27-0 ]

References: [1]Organic Preparations and Procedures International,1992,vol. 24,p. 520 - 522.

29
[ 41014-43-1 ]
[ 123-11-5 ]
[ 71907-23-8 ]

References: [1]Organic Preparations and Procedures International,1992,vol. 24,p. 520 - 522.

30
[ 41014-43-1 ]
[ 123-08-0 ]
4-(benzo[d]oxazol-2-ylmethoxy)benzaldehyde [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
34%	With potassium carbonate; In acetone; for 4h;Reflux;	General procedure: To a solution of various substituted phenols (1 mmol) in dry acetone (30 mL) K2CO3 (1 mmol)and compound 3 or 4 (1 mmol) were added. After being stirred for 4 h at reflux temperature, thereaction mixture was cooled, filtered, and concentrated under vacuum. Then the residue was dilutedwith 30 mL ethyl acetate and sequentially washed with 30 mL 1 M HCl, aq. NaHCO3 solution andbrine in order. The organic layer was dried over MgSO4 and concentrated in vacuo. Purification of theresidue by chromatography on silica gel furnished target compounds. 1H-NMR, 13C-NMR and massspectroscopy (MS) of compounds 5a-m and 6a-m are shown in Supplementary Materials.

References: [1]Molecules,2018,vol. 23.
[2]Journal of Medicinal Chemistry,2000,vol. 43,p. 690 - 705.

31
[ 41014-43-1 ]
[ 131242-36-9 ]
2-[(2-Pyrimidinylthio)methyl]benzoxazole [ No CAS ]

References: [1]Journal of Fluorine Chemistry,2000,vol. 102,p. 369 - 376.
[2]Journal of Fluorine Chemistry,2001,vol. 109,p. 39 - 48.

32
[ 41014-43-1 ]
[ 119-61-9 ]
[ 35491-33-9 ]

References: [1]Synthetic Communications,2003,vol. 33,p. 3551 - 3559.

33
[ 41014-43-1 ]
[ 591-78-6 ]
1-benzooxazol-2-yl-2-methyl-hexan-2-ol [ No CAS ]

References: [1]Synthetic Communications,2003,vol. 33,p. 3551 - 3559.

34
[ 41014-43-1 ]
[ 152298-09-4 ]

References: [1]Synthetic Communications,2003,vol. 33,p. 1433 - 1442.

35
[ 41014-43-1 ]
[ 108-94-1 ]
[ 35491-36-2 ]

References: [1]Synthetic Communications,2003,vol. 33,p. 3551 - 3559.

Historical Records

Technical Information

• Alkyl Halide Occurrence • General Reactivity • Grignard Reaction • Hiyama Cross-Coupling Reaction • Kinetics of Alkyl Halides • Kumada Cross-Coupling Reaction • Reactions of Alkyl Halides with Reducing Metals • Reactions of Amines • Stille Coupling • Substitution and Elimination Reactions of Alkyl Halides • Suzuki Coupling

Related Functional Groups of
[ 41014-43-1 ]

Chlorides

A243940 [63816-18-2]

6-Chloro-2-methylbenzo[d]oxazole

Similarity: 0.83

A127524 [323579-00-6]

2-Methyl-5-chloro-6-benzoxazolamine

Similarity: 0.81

A137169 [17200-29-2]

5-Chlorobenzoxazole

Similarity: 0.74

A194342 [615-18-9]

2-Chlorobenzoxazole

Similarity: 0.72

A268528 [27383-92-2]

Methyl 5-chlorobenzo[d]oxazole-2-carboxylate

Similarity: 0.71

Related Parent Nucleus of
[ 41014-43-1 ]

Benzoxazoles

A150889 [5676-60-8]

2-Methylbenzo[d]oxazol-6-amine

Similarity: 0.88

A425088 [23997-94-6]

2-Methylbenzo[d]oxazol-5-ol

Similarity: 0.87

A141850 [77186-95-9]

Benzo[d]oxazol-2-ylmethanol

Similarity: 0.85

A243940 [63816-18-2]

6-Chloro-2-methylbenzo[d]oxazole

Similarity: 0.83

A100367 [5676-58-4]

2,5-Dimethylbenzoxazole

Similarity: 0.82

Precautionary Statements-General
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P322
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P378
P380	Evacuate area.
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P304 + P340	IF INHALED: Remove victim to fresh air and Keep at rest in a position comfortable for breathing.
P304 + P341	IF INHALED: If breathing is difficult, remove victim to fresh air and keep at rest in a position comfortable for breathing.
P305 + P351 + P338	IF IN EYES: Rinse cautiously with water for several minutes. Remove contact lenses, if present and easy to do. Continue rinsing.
P306 + P360	IF ON CLOTHING: Rinse Immediately contaminated CLOTHING and SKIN with plenty of water before removing clothes.
P307 + P311	IF exposed: call a POISON CENTER or doctor/physician.
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P332 + P313	IF SKIN irritation occurs: Get medical advice/attention.
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P335 + P334	Brush off loose particles from skin. Immerse in cool water/wrap in wet bandages.
P337 + P313	IF eye irritation persists: Get medical advice/attention.
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Storage
Code	Phrase
P401
P402	Store in a dry place.
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P402 + P404	Store in a dry place. Store in a closed container.
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Disposal
Code	Phrase
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Physical hazards
Code	Phrase
H200	Unstable explosive
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H202	Explosive; severe projection hazard
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Health hazards
Code	Phrase
H300	Fatal if swallowed
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H310	Fatal in contact with skin
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H371	May cause damage to organs
H372	Causes damage to organs through prolonged or repeated exposure
H373	May cause damage to organs through prolonged or repeated exposure
Environmental hazards
Code	Phrase
H400	Very toxic to aquatic life
H401	Toxic to aquatic life
H402	Harmful to aquatic life
H410	Very toxic to aquatic life with long-lasting effects
H411	Toxic to aquatic life with long-lasting effects
H412	Harmful to aquatic life with long-lasting effects
H413	May cause long-lasting harmful effects to aquatic life
H420	Harms public health and the environment by destroying ozone in the upper atmosphere

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CAS No.: 41014-43-1

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