Water → N-(1-Chlorobutan-2-yl)acetamide

Participants

Reaction Conditions

Reaction Steps

A 500 ml. 3-necked flask fitted with a stirrer and dry ice-acetone trap is charged with 82.1 g. (2.0 mole) acetonitrile, 27.4 g. (1.52 mole) water, 27 g. (0.25 mole) Na2CO3 and 28.1 g. (0.50 mole) 1-butene and cooled to 0° C. Chlorine (0.50 mole) is added over one-half hour, the reaction temperature reaching a high of 32° C. After stirring for 2 hours at 25° C., the reaction mixture is filtered. The acetonitrile washings of the solid phase and filtrate is combined and the solvents removed by vacuum distillation to leave 33.0 g. of the N-[1-(chloromethyl)propyl]acetamide (44.0% yield based on 1-butene).

Provenance & Evidence