2-Chloroethyl isocyanate → 1-(p-Acetamidophenyl)-3-(2-chloroethyl) urea

Participants

Reaction Steps

A solution of 1800 g of p-aminoacetanilide in 7000 ml of dimethylformamide is stirred at room temperature. The solution is then cooled to 10°-15° in an ice-water bath. To the stirred cooled solution is added 1440 g of 2-chloroethyl isocyanate in a thin stream over a 50-minute period, keeping the reaction mixture temperature between 20° and 25°. The reaction mixture is stirred at room temperature for 90 minutes; 8000 ml of ice-water is added over a 20-minute period. After stirring for an additional 2 hours, the solid is filtered off and washed with 4000 ml of water. The crude product is slurried with 7000 ml of 95% alcohol. The solid is filtered off and air-dried overnight at room temperature to give 1-(p-acetamidophenyl)-3-(2-chloroethyl)-urea, m.p. 207°-9° dec.

Provenance & Evidence