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

HRID 904346
Notes
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Reaction equation

HRID 904346 reaction equation
[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]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 3

HCID 66133
Benzyl triethylammonium chloride
Catalyst
HCID 962WaterSolvent
HCID 6344DichloromethaneSolvent

Conditions

Temperature
25 °C

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-5caf51a52b2143258a8e055037917d65
Source dataset
uspto-grants-1980_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04230875

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes