Dimethylamine → N,N-dimethyl-4-(hexadecylamino)benzamide

Participants

Reaction Steps

In a solution of 100 ml. of methylene dichloride and 25 ml. of glyme was dissolved in 10 ml. of thionyl chloride and 4.0 g. of 4-(n-hexadecylamino)benzoic acid hydrochloride. The reaction mixture was heated to the reflux temperature for 2 hours and then cooled to room temperature. To this solution of acid chloride was added a solution of 200 ml. of diethyl ether, 25 ml. of glyme, and 0.1 g. of 4-dimethylaminopyridine which had been saturated with dimethylamine gas. This reaction mixture was stirred at room temperature for 2 hours whereby there was obtained a 92% yield of product, melting point 70°-72° C.

Provenance & Evidence