1-(p-Acetamidophenyl)-3-(2-chloroethyl) urea → N-[4-(2-Oxoimidazolidin-1-yl)phenyl]acetamide

Participants

Reaction Steps

A mixture of 1600 g of 1-(p-acetamidophenyl)-3-(2-chloroethyl) urea in 7200 ml of dimethylformamide is stirred at room temperature under an atmosphere of nitrogen. To the resulting solution is added a solution of 400 g of sodium methoxide in 2000 ml of methyl alcohol (anhydrous) in a thin stream over a 90-minute period. The temperature rises during the addition. The reaction mixture is stirred for an additional 20 minutes and then heated to 70°-75° and kept at this temperature for 1 hour. The reaction mixture is then allowed to cool slowly to 32° over a period of about 3 hours with stirring; 5000 ml of ice-water is then added rapidly. Stirring at room temperature is continued for 4 hours and the mixture is allowed to stand at room temperature overnight. The solid is filtered off and washed with 3000 ml of water and air-dried for about 2 days at room temperature to give 1-(p-acetamidophenyl)-2-imidazolidinone, m.p. 270°-273°.

Provenance & Evidence