[C:1]([CH2:3][NH:4][C:5](=[O:11])[C:6]([Cl:10])=[C:7]([Cl:9])[Cl:8])#[N:2].[Cl:12][C:13]([Cl:19])([S:17]Cl)[CH:14]([Cl:16])[Cl:15].N1C=CC=CC=1.C(N(CC)CC)C>C(Cl)Cl>[C:1]([CH2:3][N:4]([S:17][C:13]([Cl:19])([Cl:12])[CH:14]([Cl:16])[Cl:15])[C:5](=[O:11])[C:6]([Cl:10])=[C:7]([Cl:8])[Cl:9])#[N:2]
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.
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