1,1,2,2-Tetrachloroethylsulfenyl chloride → HCID 13799794, compound

A stirred mixture of 2.38 g (0.01 moles) N-(2-cyano-2-propyl)-2-methylsulfinylethylsulfonamide (Example 29), 2.85 g (0.0109 moles) of 89.9% technical 1,1,2,2-tetrachloroethylsulfenyl chloride and a catalytic amount (about 0.25 g) of benzyltriethylammonium chloride in 30 ml methylene chloride was warmed until a solution was obtained. To that mixture, 0.96 g of a 50% solution of sodium hydroxide which had been diluted to 5 ml was added at once. The reaction mixture was stirred at reflux for four hours, then cooled and poured into a separatory funnel. The methylene chloride layer was separated, washed three times with 25 ml water, dried and evaporated to about 10 ml. The oily residue was transferred to a 50 ml Erlenmeyer flask and then diluted with about 25 ml hexane. The white precipitate which formed was recovered by filtration and washed with hexane to give 2.85 g of a white powder. Chromatography on silica gel, followed by recrystallization from ethanol gave 1.7 g of the above-identified product as white crystals, melting point 119°-120° C.

1. customwas obtained
2. additionwas added at once
3. temperatureat reflux for four hours
4. temperaturecooled
5. additionpoured into a separatory funnel
6. customThe methylene chloride layer was separated
7. washwashed three times with 25 ml water
8. customdried
9. customevaporated to about 10 ml
10. additiondiluted with about 25 ml hexane
11. customThe white precipitate which formed
12. filtrationwas recovered by filtration
13. washwashed with hexane

ORD record

ord-9d7e5f9e46714f45a0bc73d05506a027

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04652556