Hydrochloric Acid → 3-Cyano-N,N-dimethylbenzamide

Participants

Reaction Steps

A mixture of 85.22 g of m-cyanobenzoic acid, 400 ml of toluene, 4.48 ml (4.23 g) of N,N-dimethylformamide and 44.4 ml (72.3 g) of thionyl chloride was gently heated on a steam bath for 2 hours with sulfur dioxide and hydrogen chloride being evolved. The reaction solution was cooled in an ice bath and cautiously added portionwise, over one hour, to stirred and cooled solution of 250 ml of 40% aqueous diethylamine and 100 ml of water. At intervals 2-3 ml of concentrated aqueous potassium hydroxide was added. After the addition was complete, the mixture was stirred for several hours, then the layers were separated and the organic layer washed with water. After permitting the organic layer to evaporate to dryness, the residue was recrystallized from 300 ml of ethanol containing charcoal, giving 68.5 g of the desired compound as white crystals, mp 85°-88° C.

Provenance & Evidence