1,1,2,2-Tetrachloroethylsulfenyl chloride → HCID 12894656, compound

HRID 1703065Notes

Reaction equation

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

Participants

Conditions

Temperature: 25 °C

Procedure

A 3.8 g (0.047 mol) sample of 50% weight aqueous sodium hydroxide solution was added dropwise to a cooled (8° C.) solution of 9.0 g (0.043 mol) N-hexyl propanesulfonamide and 11.0 g (0.047 mol) 1,1,2,2-tetrachloroethylsulfenyl chloride in 150 ml dichloromethane. After the addition was completed, the reaction was stirred at about 25° C. for 4 hours during which time a precipitate formed. The reaction mixture was then washed with water, dried over magnesium sulfate and evaporated under reduced pressure to give an oily residue. The residue was chromatographed through 250 g silica gel with 10% ethylether/90% hexane elution to give 7 g of the product as a yellow oil. The elemental analysis for the product showed: %S, calc. 15.8, found 16.2; %Cl, calc. 35.0, found 33.5. The product is tabulated in Table I as Compound No. 1.

Workup

additionAfter the addition
customformed
washThe reaction mixture was then washed with water
dry with materialdried over magnesium sulfate
customevaporated under reduced pressure
customto give an oily residue
customThe residue was chromatographed through 250 g silica gel with 10% ethylether/90% hexane elution

Sources & evidence

ORD record: ord-755ed3df318f48309f4d71ee12c18dc7
Source dataset: uspto-grants-1982_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US04350831

Reaction notes

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