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

HRID 1763686Notes

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]

Participants

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

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

Sources & evidence

ORD record: ord-f24d1545c41943158f5da8c9ee233cd1
Source dataset: uspto-grants-1978_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04112237

Reaction notes

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