Chloroacetamide | 2-Chloroacetamide | Chlorides

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Product Details of Chloroacetamide

CAS No. :	79-07-2
Formula :	C₂H₄ClNO
M.W :	93.51
SMILES Code :	O=C(N)CCl
Synonyms :	2-Chloroacetamide
MDL No. :	MFCD00008027
InChI Key :	VXIVSQZSERGHQP-UHFFFAOYSA-N
Pubchem ID :	6580

Safety of Chloroacetamide

GHS Pictogram:
Signal Word:	Danger
Hazard Statements:	H301-H317-H361-H402
Precautionary Statements:	P501-P261-P273-P272-P270-P202-P201-P264-P280-P302+P352-P308+P313-P362+P364-P333+P313-P301+P310+P330-P405
Class:	6.1
UN#:	2811
Packing Group:	Ⅲ

Application In Synthesis of Chloroacetamide

* 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.

Upstream synthesis route of [ 79-07-2 ]
Downstream synthetic route of [ 79-07-2 ]

[ 79-07-2 ] Synthesis Path-Upstream 1~2

1
[ 120-83-2 ]
[ 79-07-2 ]
[ 27320-99-6 ]

References: [1] Journal of the Korean Chemical Society, 2012, vol. 56, # 4, p. 468 - 472,5.
[2] Journal of the Korean Chemical Society, 2012, vol. 56, # 4, p. 468 - 472.

2
[ 121-33-5 ]
[ 79-07-2 ]
[ 186685-89-2 ]

Yield	Reaction Conditions	Operation in experiment
86%	With potassium carbonate In N,N-dimethyl-formamide; acetonitrileReflux	General procedure: A mixture of the corresponding halide (0.010 mol), hydroxybenzaldehyde (0.011 mol), and potassium carbonate (2.00 g, 0.0145 mol) in a mixture of acetonitrile-DMF (20 mL, 8 : 2, v/v) was refluxed for 5-7 h with stirring (TLC monitoring). After evaporation of the solvents, the residue was treated with water, a precipitate formed was filtered off, washed with 30percent aqueous methanol, and dried in air. Yields and physicochemical characteristics of aldehydes 9-12 are given in Table 4.

References: [1] Russian Chemical Bulletin, 2015, vol. 64, # 2, p. 395 - 404[2] Izv. Akad. Nauk, Ser. Khim., 2015, # 2, p. 395 - 404,10.
[3] Russian Journal of General Chemistry, 2005, vol. 75, # 7, p. 1113 - 1124.
[4] European Journal of Medicinal Chemistry, 2014, vol. 81, p. 1 - 14.

[ 79-07-2 ] Synthesis Path-Downstream 1~13

1
[ 3847-57-2 ]
[ 79-07-2 ]
[ 64649-40-7 ]

References: [1]Chemische Berichte,1985,vol. 118,p. 2777 - 2788.

2
[ 124-38-9 ]
[ 79-07-2 ]
[ 2346-26-1 ]

References: [1]Tetrahedron,1995,vol. 51,p. 5891 - 5900.

3
[ 116548-04-0 ]
[ 79-07-2 ]
2-(3-Cyano-6-trifluoromethyl-pyridin-2-yloxy)-acetamide [ No CAS ]

References: [1]Journal of Fluorine Chemistry,1996,vol. 78,p. 21 - 25.

4
[ 17351-61-0 ]
[ 79-07-2 ]
[ 2346-26-1 ]

References: [1]Tetrahedron,1999,vol. 55,p. 193 - 200.

5
[ 36822-11-4 ]
[ 79-07-2 ]
[ 56605-38-0 ]

References: [1]Zeitschrift fur Naturforschung, B: Chemical Sciences,1999,vol. 54,p. 788 - 798.

6
[ 6092-47-3 ]
alcoholic NH₃ [ No CAS ]
[ 79-07-2 ]

References: [1]Canadian Journal of Research,1933,vol. 8,p. 453.
Chemisches Zentralblatt,1933,vol. 104,p. 1021.

7
[ 79-07-2 ]
[ 5325-64-4 ]

Yield	Reaction Conditions	Operation in experiment
	With methylamine;	EXAMPLE 87 PREPARATION OF alpha-CHLOROACETYLSARCOSINAMIDE Sarcosinamide hydrochloride was prepared by reacting methylamine with 2-chloroacetamide as described by Marvel et al. (1946). The compound was recrystallized from ethanol. Mp 160-161 C.

References: [1]Patent: US5073641,1991,A .

8
[ 1059630-08-8 ]
[ 79-07-2 ]
[ 1059630-09-9 ]

Yield	Reaction Conditions	Operation in experiment
	With N-ethyl-N,N-diisopropylamine; potassium iodide; In acetonitrile; for 27.0h;Heating / reflux;	Example 4: Production of [4aS,9bR] -ethyl 5-(2-amino-2-oxoethyl)-6-bromo- 3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole-2(9bH)-carboxylate; (4aS,9bR)-ethyl 5-(2-amino-2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro- lH-pyrido[4,3-b]indole-2(9bH)-carboxylate may be prepared by heating to a reflux a suspension of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro- 1 H-pyrido[4,3-b]indole- 2(9bH)-carboxylate (5.648g, 17.4mmol), 2-chloroacetamide (7.32g, 78.2mmol), potassium iodide (19.2g, 77.7mol) and diisopropylethylamine (19mL, 115mmol) in acetonitrile (8OmL) for 27 hours. The solvent is removed in a vacuo and water <n="88"/>(20OmL) is added to the residue and stirred for 1 hour. The resulting white solid is filtered off, washed with ethanol and dried.
	With N-ethyl-N,N-diisopropylamine; potassium iodide; In acetonitrile; for 27.0h;Reflux;	(4aS,9bR)-ethyl 5-(2-amino-2-oxoethyl)-6-bromo-3,4,4a,5-tetrahydro-lH- pyrido[4,3-b]indole-2(9bH)-carboxylate may be prepared by heating to a reflux a suspension of (4aS,9bR)-ethyl 6-bromo-3,4,4a,5-tetrahydro-lH-pyrido[4,3-b]indole- 2(9bH)-carboxylate (5.648g, l7.4mmol), 2-chloroacetamide (7.32g, 78.2mmol), potassium iodide (19.2g, 77.7mol) and diisopropylethylamine (l9mL, H5mmol) in acetonitrile (80mL) for 27 hours. The solvent is removed in a vacuo and water (200mL) is added to the residue and stirred for 1 hour. The resulting white solid is filtered off, washed with ethanol and dried.

References: [1]Patent: WO2008/112280,2008,A1 .Location in patent: Page/Page column 86-87.
[2]Drugs of the Future,2015,vol. 40,p. 643 - 650.
[3]Patent: WO2019/241278,2019,A1 .Location in patent: Paragraph 000116.

9
[ 13589-72-5 ]
[ 79-07-2 ]
[ 1169561-46-9 ]

References: [1]Bioorganic and Medicinal Chemistry Letters,2012,vol. 22,p. 3727 - 3731.

10
[ 20146-59-2 ]
[ 79-07-2 ]
[ 1380598-38-8 ]

Yield	Reaction Conditions	Operation in experiment
96%	With potassium carbonate; In N,N-dimethyl-formamide; at 20℃; for 18h;	General procedure: To a solution of starting <strong>[20146-59-2]4-chloro-1H-quinolin-2-one</strong>s (0.005 mol, 1e, 1.045 g) in 40 mL of DMF and K2CO3, chloroacetamide (0.01 mol) or ethylchloroacetate (0.01 mol) was added. The resulting solution was stirred at room temperature for 14-18 h. After completion of the reaction, it was checked by TLC, and the mixture was poured into crushed ice and then filtered, dried. The mixture was purified by column chromatography using petroleum ether and ethyl acetate (95:5) as eluent.

References: [1]Tetrahedron Letters,2012,vol. 53,p. 3230 - 3232.

11
[ 90-15-3 ]
[ 79-07-2 ]
[ 86-86-2 ]

References: [1]Journal of Medicinal Chemistry,2013,vol. 56,p. 7851 - 7861.

12
[ 22680-44-0 ]
[ 79-07-2 ]
N-(o-chlorobenzyl)iminodiacetamide [ No CAS ]

Yield	Reaction Conditions	Operation in experiment
61%	With sodium carbonate; potassium iodide; In water; at 80℃;pH Ca. 5 - 6;Heating;	General procedure: Typically, 1.66 g (0.01 mol) potassium iodide and 0.05 molbenzylammonium chloride [Note 1] were added to a hot aqueous solution (ca. 80C) of 10.0 g chloroacetamide (0.11 mol in 100mL) in a 500-mL Erlenmeyer flask. Then, 1.25 g (0.012 mol) sodium carbonate was added in small portions while shaking the flask [CAUTION - foaming] in order to partially deprotonate the benzylammonium cation. After the effervescence has subsided, the reaction mixture was heated to boiling and set aside for 30 min [Note 2]. A second portion of 1.25 g sodium carbonate (0.012 mol) was then added; the reaction mixture was heated to boiling and set aside for 20 min. This addition of sodium carbonate-boiling-20 min waiting procedure was repeated three more times (five 1.25 g portions of sodium carbonate were added in total), after which the products started to crystallize upon spontaneous cooling of the hot solutions [Note 3]. After the reaction mixtures were left to stand overnight, the products were filtered off by suction, washed with ice-cold water (100 mL), dried by standing in air and protected from direct sunlight [Note 4]. Note 1. The corresponding benzylammonium chlorides were prepared from benzyl halides via the Reichert-Dornis modification of Delepine reaction. [17] N-Benzylhexamethylene tetraminium halides were prepared by mixing the solutions of hexamethylenetetramine and benzyl halide in chloroform, then filtered off by suction, washed with small volumes of chloroform,and air-dried as described. [18] These salts were dissolved or suspended in water, and the reaction mixtures were saturated with sulfur dioxide. The precipitated N-benzylaminomethylsulfites were filtered off by suction, washed with water, andair-dried. [17] Cleavage of N-benzylaminomethylsulfites into benzylammonium chlorides was performed by boiling with diluted hydrochloric acid (1 : 1 v/v). After the reaction mixtures were evaporated to a small volume, the desired benzylamine hydrochlorides crystallized in almost quantitative yields. All these reactions were performed in a fume cupboard. Note 2. The reaction mixture should be slightly acidic (pH ca. 5-6) before each addition of sodium carbonate. Some times, the products start to crystallize before the final step. In that case, the reaction mixture should be heated to dissolve the product before further addition of sodium carbonate. Note 3. The total amount of sodium carbonate is lower than required for complete neutralization of the acid released during the reaction. The final solution has to be acidic to keep the unreacted amine in its protonated (soluble) form, which is easily removed from the product by simple washing with water. The addition of the sixth 1.25 g portion of sodium carbonate did not improve the yield significantly, however, gave impure, yellow and vile smelling products contaminated with the starting amines. Note 4. The products are obtained in the form of white crystals and are sufficiently pure to be used as complexing agents. They should be stored in dark bottles because they usually become yellow upon exposure to sunlight.

References: [1]Australian Journal of Chemistry,2016,vol. 69,p. 896 - 904.

13
[ 79-37-8 ]
[ 64-17-5 ]
[ 79-07-2 ]
[ 6092-47-3 ]

Yield	Reaction Conditions	Operation in experiment
95%		General procedure: To a solution of 2-chloroacetamide (1.70 g, 18.2 mmol) in anhydrous 1,2-dichloroethane (20 mL)was added oxalyl chloride (2 mL) at 0 C, then refluxed in an oil bath at 90 C for 4 h. The reactionmixture was then cooled to 0 C, and alcohol or amine (18.2 mmol) was added into the reaction mixture.The reaction mixture was stirred for another 5 min. Upon completion, the solid was filtrated andwashed with 1,2-dichloroethane to give 3a-3j [39].

References: [1]Molecules,2020,vol. 25.

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Product Details of Chloroacetamide

Safety of Chloroacetamide

Application In Synthesis of Chloroacetamide

[ 79-07-2 ] Synthesis Path-Upstream 1~2

[ 79-07-2 ] Synthesis Path-Downstream 1~13

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