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

HRID 2419777노트

반응식

HRID 2419777 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 66133Benzyl triethylammonium chloride촉매HCID 6344Dichloromethane용매

실험 절차

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 mcl) 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 1 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.

후처리

  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

출처 및 근거

ORD 기록
ord-1bf8b25b380b42debf4ff85fec9ccddc
출처 데이터셋
uspto-grants-1978_08
특허 번호
US04107332

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