79-07-2

white crystalline powder

A component of herbicidal mixtures of cellulose biosynthesis inhibitors with VLCFA inhibitors.

Chloroacetamide is a preservative used in several applications such as in cutting metalwork fluids, in paints or in glues. It can induce contact dermatitis in hairdressers, or in shoemakers when used as a leather preservative.

Nonflammable

Chloroacetamide can be prepared from chloroacetyl chloride and dry ammonia gas and by treating ethyl chloroacetate or methyl chloroacetate with cold aqueous ammonia solutions in a 2-l. A 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. Vigorous stirring is started, and 200 cc. of chilled aqueous ammonia (sp. gr. 0.9) is added to the cold ester. The solution is stirred in the cold for about fifteen minutes, then another 200. A 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℃ is 128–138 g. 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 Chloroacetamide is obtained. The recrystallized product melts at 119–120°.

Recrystallise the amide from acetone and dry it under vacuum over P2O5. [Beilstein 2 IV 490.]