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

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.

1. additionA mixture of 5.0 g
2. customto give a clear solution
3. temperatureThe resulting mixture was cooled in an ice bath
4. customThe ice bath was removed
5. customthe course of the reaction)
6. temperatureThe reaction mixture was cooled again in an ice bath
7. stirringthe mixture was stirred for one hour
8. customto give an oil
9. customThe oil was chromatographed on a column of 165 g silica gel
10. washeluted with benzene

ORD record

ord-e502c52722194a08bcaad943e5a6f39a

Source dataset

uspto-grants-1988_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04785019