Triethylamine → HCID 10883497, compound

Participants

Reaction Steps

A solution of N-(2,2,2-trifluoroethyl)-3,5-dichlorobenzimidoyl chloride (8.72 g, 0.03 mol) in N,N-dimethylformamide is treated with 2-chloroacrylonitrile (3.0 g, 0.0345 mol) under a nitrogen atmosphere. Triethylamine (9.56 g, 0.0945 mol) is added slowly at 50° C. over two hours and the reaction mixture is stirred at 58°-60° C. for 18 hours. Bromine (4.8 g, 0.03 mol) is then added over 20 minutes as the temperature rises from 25° C. to 36° C. The resultant reaction mixture is diluted with water and extracted with methylene chloride. Evaporation and flash column chromatography using silica gel and a 20% ethyl acetate in heptane solution gives the title product as a white crystalline solid (5.4 g, 46.9% yield) which is identified by 19F and 1H NMR.

Provenance & Evidence