1,1,2,2-Tetrachloroethylsulfenyl chloride → HCID 13799793, compound

To a stirred mixture of 3.53 g (0.0159 moles) N-(2-cyano-2-propyl)-2-(methylthio)ethylsulfonamide (the product of Example 27), 4.15 g of 89.9% 1,1,2,2-tetrachloroethylsulfenyl chloride (3.74 g [0.0159] moles) and about 1 g benzyltriethylammonium chloride in 25 ml methylene chloride, 0.8 g (0.02 l mole) sodium hydroxide in 5 ml water was added. The reaction mixture was stirred at room temperature for 18 hours. The layers were separated using a separatory funnel. The methylene chloride layer was washed three times with 30 ml water, dried and concentrated on a rotovap to about 20 ml. Hexane was added to the solution until turbidity. The mixture was warmed until clear. Cooling of the mixture gave a white powder which was isolated by filtration and then washed with hexane to give 2.4 g of crude product. A second crop of 1.8 g of crude product was obtained from the filtrate. The two crops were combined and recrystallized from ethanol to give 2.2 g of the above-identified product as a solid, melting point 83°-84° C. A second crop of 1.1 g solid was obtained.

1. additionwas added
2. customThe layers were separated
3. washThe methylene chloride layer was washed three times with 30 ml water
4. customdried
5. concentrationconcentrated on a rotovap to about 20 ml
6. additionHexane was added to the solution until turbidity
7. temperatureThe mixture was warmed until clear
8. temperatureCooling of the mixture
9. customgave a white powder which
10. customwas isolated by filtration
11. washwashed with hexane
12. customto give 2.4 g of crude product
13. customA second crop of 1.8 g of crude product was obtained from the filtrate
14. customrecrystallized from ethanol

ORD record

ord-59721e0c109746e7ada073841f834335

Source dataset

uspto-grants-1987_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US04652556