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

HRID 1703066Notes

Reaction equation

HRID 1703066 reaction equation
[OH-].[Na+].[CH:3]1([NH:9][S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH2:8][CH2:7][CH2:6][CH2:5][CH2:4]1.[Cl:16][C:17]([Cl:23])([S:21]Cl)[CH:18]([Cl:20])[Cl:19]>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.C(Cl)Cl>[CH:3]1([N:9]([S:21][C:17]([Cl:23])([Cl:16])[CH:18]([Cl:20])[Cl:19])[S:10]([CH:13]([CH3:15])[CH3:14])(=[O:12])=[O:11])[CH2:4][CH2:5][CH2:6][CH2:7][CH2:8]1

Participants

6

Reactant 3

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14798Sodium HydroxideHCID 13053802N-cyclohexyl-isopropanesulfonamide

Product 1

HCID 12894681N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)-isopropanesulfonamideYield 37%

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 6344DichloromethaneSolvent

Procedure

A 2.4 g (0.29 mol) sample of 50% weight aqueous sodium hydroxide solution was added dropwise to a cooled (12° C.) solution of 5.6 g (0.027 mol) N-cyclohexyl-isopropanesulfonamide, 7 g (0.029 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride and 0.5 g benzyl triethylammonium chloride in 150 ml methylene chloride. A precipitate formed in the reaction mixture during the first 10 minutes of the addition. After the addition was completed, the reaction mixture was allowed to warm to room temperature and stirred for one hour. The reaction mixture was then washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give the reaction product. The reaction product was chromatographed through 250 g silica gel with 50% chloroform/50% hexane elution to give 4 g (37%) of N-cyclohexyl-N-(1,1,2,2-tetrachloroethylthio)-isopropanesulfonamide, m.p. 122°-123° C. This reaction is tabulated in Table II as Run No. 1.

Workup

  1. customA precipitate formed in the reaction mixture during the first 10 minutes of the addition
  2. additionAfter the addition
  3. washThe reaction mixture was then washed with water
  4. dry with materialdried over magnesium sulfate
  5. customevaporated under reduced pressure
  6. customto give the reaction product
  7. customThe reaction product was chromatographed through 250 g silica gel with 50% chloroform/50% hexane elution

Sources & evidence

ORD record
ord-445d521a12434525935fff6fb0138863
Source dataset
uspto-grants-1982_09
Patent number
US04350831

Reaction notes

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