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

HRID 1834041Notes

Reaction equation

HRID 1834041 reaction equation
[CH:1]1([NH:7][S:8]([CH2:11][Br:12])(=[O:10])=[O:9])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[Cl:13][C:14]([Cl:20])([S:18]Cl)[CH:15]([Cl:17])[Cl:16]>C(N(CC)CC)C>[CH:1]1([N:7]([S:18][C:14]([Cl:20])([Cl:13])[CH:15]([Cl:17])[Cl:16])[S:8]([CH2:11][Br:12])(=[O:10])=[O:9])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

4

Reactant 2

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 20563809HCID 20563809, compound

Product 1

HCID 12803020N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)-bromomethanesulfonamide

Reagents, catalysts & solvents 1

HCID 8471TriethylamineSolvent

Procedure

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.

Workup

  1. additionAfter the addition
  2. temperatureunder reflux for 2 hours
  3. temperatureThe reaction mixture was then cooled
  4. washwashed with water
  5. dry with materialdried over magnesium sulfate
  6. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-c522a82d9db54e288ea327a74a6223e2
Source dataset
uspto-grants-1978_01
Patent number
US04068000

Reaction notes

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