1,1,2,2-Tetrachloroethylsulfenyl chloride → N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)-bromomethanesulfonamide

Participants

Reaction Steps

A 5.1 g (0.051 mol) sample of triethylamine was added dropwise to a cooled (20° C) solution of 11 g (0.043 mol) N-cyclohexyl bromomethanesulfonamide and 10.1 g (0.043 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride. After the addition was completed, the reaction was stirred at ambient temperature for 2 hours and then under reflux for 2 hours. The reaction mixture was then cooled, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give the N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)-bromomethanesulfonamide product, which after crystallization from dioxane melted at 38°-40° C. The elemental analysis for the product is tabulated in Table I under Compound No. 8.

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