1,1,2,2-Tetrachloroethylsulfenyl chloride → N-methoxycarbonylmethyl-N-(1,1,2,2-tetrachloroethylthio)cyclohexanesulfonamide

HRID 1763686노트

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HRID 1763686 반응식
[OH-].[Na+].[CH3:3][O:4][C:5]([CH2:7][NH:8][S:9]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:11])=[O:10])=[O:6].[Cl:18][C:19]([Cl:25])([S:23]Cl)[CH:20]([Cl:22])[Cl:21]>O.[Cl-].C([N+](CC)(CC)CC1C=CC=CC=1)C.ClCCl>[CH3:3][O:4][C:5]([CH2:7][N:8]([S:23][C:19]([Cl:25])([Cl:18])[CH:20]([Cl:22])[Cl:21])[S:9]([CH:12]1[CH2:17][CH2:16][CH2:15][CH2:14][CH2:13]1)(=[O:10])=[O:11])=[O:6]

참가 물질

7

반응물 3

HCID 144531,1,2,2-Tetrachloroethylsulfenyl chlorideHCID 14798Sodium HydroxideHCID 20575296N-(methoxycarbonylmethyl)cyclohexanesulfonamide

생성물 1

HCID 20575290N-methoxycarbonylmethyl-N-(1,1,2,2-tetrachloroethylthio)cyclohexanesulfonamide수율 19.2%

시약·촉매·용매 3

HCID 66133Benzyl triethylammonium chloride촉매HCID 962Water용매HCID 6344Dichloromethane용매

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온도
25 °C

실험 절차

A 1.2 g (0.03 mol) sample of sodium hydroxide in 1.2 ml water was added dropwise to a solution of 6.5 g (0.03 mol) N-(methoxycarbonylmethyl)cyclohexanesulfonamide, 7.0 g (0.03 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride, 0.5 g. triethylbenzylammonium chloride in 100 ml dichloromethane. The resulting reaction mixture was stirred at about 25° C. for 3 hours, washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give an oil residue. The residue was chromatographed through silica gel. Elution with 10% ethyl ether/hexane gave 2.5 g of the product as an oil. Elemental analysis for C11H17Cl4NO4S2 showed: %Cl, calc. 32.7, found 32; %S, calc. 14.8, found 15.1. The product is tabulated in Table I as Compound No. 2.

후처리

  1. customThe resulting reaction mixture
  2. washwashed with water
  3. dry with materialdried over magnesium sulfate
  4. customevaporated under reduced pressure
  5. customto give an oil residue
  6. customThe residue was chromatographed through silica gel
  7. washElution with 10% ethyl ether/hexane

출처 및 근거

ORD 기록
ord-f24d1545c41943158f5da8c9ee233cd1
출처 데이터셋
uspto-grants-1978_09
특허 번호
US04112237

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