Acetonitrile → 4-Chloro-N-methyl-3-nitro-N-octadecylbenzamide

Participants

Reaction Steps

102.7 g of 3-nitro-4-chlorobenzoic acid was mixed with 800 ml of acetonitrile, and thereto was added 68.6 g of thionyl chloride. The resulting mixture was heated under reflux for 4 hours, and thereto was added 63.5 g of triethylamine. After controlling the temperature of the reaction system to 5° C., a chloroform solution containing 148.6 g of methyloctadecylamine was further added dropwise. After the completion of the reaction, the reaction mixture was dispersed into water, and the organic phase was dried over anhydrous sodium sulfate. The inorganic matter was filtered out, and the solvent was distilled away. The reaction product was recrystallized from a 1:3 mixture of acetonitrile and methanol. Yield: 186 g, Percent yield: 76.0%, Melting point: 55°-56° C.

Provenance & Evidence