Triethylamine → N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)trichlorovinylsulfonamide

HRID 971648Notes

Reaction equation

C(N(CC)CC)C.[CH:8]1([NH:14][S:15]([C:18]([Cl:22])=[C:19]([Cl:21])[Cl:20])(=[O:17])=[O:16])[CH2:13][CH2:12][CH2:11][CH2:10][CH2:9]1.[Cl:23][C:24]([Cl:30])([S:28]Cl)[CH:25]([Cl:27])[Cl:26]>ClCCl>[CH:8]1([N:14]([S:28][C:24]([Cl:30])([Cl:23])[CH:25]([Cl:27])[Cl:26])[S:15]([C:18]([Cl:22])=[C:19]([Cl:20])[Cl:21])(=[O:17])=[O:16])[CH2:9][CH2:10][CH2:11][CH2:12][CH2:13]1

Participants

Conditions

Temperature: 25 °C

Procedure

A 4.0 g (0.04 mol) sample of triethylamine was added dropwise to a cooled (-10° to 0° C.) solution of 9.5 g (0.0324 mol) N-(cyclohexyl)trichlorovinylsulfonamide, m.p. 152°-153° C., and 7.6 g (0.0324 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride in 200 ml dichloromethane. The reaction mixture was then stirred at about 25° C. for 3 hours, washed with water, dried over magnesium sulfate and evaporated to give an oil. The oil was chromatographed on silica gel. The N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)trichlorovinylsulfonamide product, 11 g (72% yield), was eluted from the silica gel with 30% ether/20% hexane. The infrared spectrum of the product showed strong absorption bands at 1385 cm-1 and 1160 cm-1. The elemental analysis for the product is tabulated in Table I under Compound No. 6.

Workup

washwashed with water
dry with materialdried over magnesium sulfate
customevaporated
customto give an oil
customThe oil was chromatographed on silica gel
washThe N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)trichlorovinylsulfonamide product, 11 g (72% yield), was eluted from the silica gel with 30% ether/20% hexane
customabsorption bands at 1385 cm-1 and 1160 cm-1

Sources & evidence

ORD record: ord-9af11b39a9094ab785fe58e2f5ef11ef
Source dataset: uspto-grants-1979_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04160845

Reaction notes

Loading…