chloroacetamide

Author: Janey

Sep. 23, 2024

54

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chloroacetamide

Org. Synth. , 7, 16

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DOI: 10./orgsyn.007.

CHLOROACETAMIDE

[

Acetamide, α-chloro-

]

Submitted by W. A. Jacobs and M. Heidelberger.

Checked by C. S. Marvel and D. D. Coffman.

1. Procedure

In a

2-l. round-bottomed flask

fitted with a

mechanical stirrer

and surrounded by an

ice-salt bath

is placed

215 g. (1.75 moles) of

ethyl chloroacetate

(Note 1)

. Vigorous stirring is started, and to the cold ester

(Note 2)

200 cc. of chilled aqueous

ammonia

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(sp. gr. 0.9) is added. The solution is stirred in the cold for about fifteen minutes; then another

200-cc. portion of aqueous

ammonia

is added, and the stirring is continued for about fifteen minutes. The mixture is then allowed to stand for thirty minutes, filtered with suction, and washed with two

25-cc. portions of cold water to remove

ammonium chloride

. The yield of air-dried material melting at

118&#;119°

(Note 3)

is

128&#;138 g.

(

78&#;84

per cent of the theoretical amount).

This product contains traces of

ammonium chloride

which may be removed by crystallization from water. When

100 g.

of crude product is recrystallized from 400 cc. of water, about

80 g.

of product is obtained. The recrystallized product melts at

119&#;120°

.

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Substance search result(s) - Pollution and waste management

Additional information: This substance is on the Non-domestic Substances List (NDSL).

The manufacture or import of a substance on the NDSL may be subject to notification under the New Substances Notification Regulations (Chemicals and Polymers). Following notification, Environment and Climate Change Canada and Health Canada carry out a joint assessment process to determine whether there is a potential for adverse effects on the environment and human health.

For more information on the regulatory requirements for new chemicals and polymers, refer to the Guidance document for the New Substances Notification Regulations (Chemicals and Polymers).

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