Pyridine → N-Cyanomethyl-N-(1,1,2,2-tetrachloroethylthio) trichloroacrylamide

Participants

Reaction Steps

A mixture of 5.0 g. (0.023 moles) N-cyanomethyl trichloroacrylamide (the product of Example 21) and 5.5 g (0.023 moles) 1,1,2,2-tetrachloroethyl-sulfenyl chloride in 75 ml methylene chloride were stirred together to give a clear solution. The resulting mixture was cooled in an ice bath; then 2.2 g (0.028 moles) pyridine in 25 ml methylene chloride were added over twenty minutes. The ice bath was removed; stirring was continued for 23 hours. (TLC monitored the course of the reaction). The reaction mixture was cooled again in an ice bath. Triethylamine, 2.4 g (0.024 moles) in 25 ml methylene chloride was added over fifteen minutes; the mixture was stirred for one hour. The solvent was stripped to give an oil. The oil was chromatographed on a column of 165 g silica gel and eluted with benzene to give 5.4 g of the above-identified product which slowly solidified on standing to give a solid which liquified at 70°-75° C.

Provenance & Evidence