2,3,3-Trichloro-2-propenoyl chloride → N-cyanomethyl trichloroacrylamide

Participants

Reaction Steps

A slurry of 38.8 g (0.2 mol) trichloroacrylyl chloride and 18.5 g (0.2 mol) aminoacetonitrile hydrochloride in 150 ml chloroform was stirred and heated under reflux for 30 hours, while gases evolved and most of the hydrochloride salt dissolved. The reaction mixture was filtered while hot and the solvent evaporated under reduced pressure to give 36.1 g of N-cyanomethyl trichloroacrylamide, as an off-white solid melting at 56°-59° C. Recrystallization from benzene-hexane gave a white solid melting at 58°-60° C. Elemental analysis for C5H3Cl3N2O showed: %Cl, calc. 49.8, found 50.0.

Provenance & Evidence