Dimethyl Sulfoxide → HCID 2819125, compound

Temperature

0 °C

To a solution of 2-(4-chlorobenzenesulfonyl) acetonitrile (600 mg, 2.78 mmol) in anhydrous DMSO (8 ml) under an argon atmosphere was added carbon disulfide (212 mg, 2.78 mmol). The reaction mixture was cooled to approximately 0° C. and 2 equivalents of sodium hydride (5.56 mmol) was added in one portion. The resulting thick reaction mixture was swirled until homogeneous and allowed to warm to room temperature for one hour with stirring. The reaction mixture was cooled again to 0° C. and 2 equivalents of iodomethane (5.56 mmol) was added under argon. The reaction mixture was allowed to gradually warm to room temperature and after 18 hours deionized water was added (30 ml) and the resulting slurry was stirred for 15 minutes. The solid was collected by filtration, washed with deionized water, and dried. The crude solid product thus obtained was dissolved in 25% hexanes/chloroform and purified via flash chromatography. The resulting solution was concentrated in vacuo to provide the titled compound as a light yellow solid in 65% yield.

1. temperatureto warm to room temperature for one hour
2. temperatureThe reaction mixture was cooled again to 0° C.
3. temperatureto gradually warm to room temperature and after 18 hours
4. additionwas added (30 ml)
5. stirringthe resulting slurry was stirred for 15 minutes
6. filtrationThe solid was collected by filtration
7. washwashed with deionized water
8. customdried
9. customThe crude solid product thus obtained
10. custompurified via flash chromatography
11. concentrationThe resulting solution was concentrated in vacuo

ORD record

ord-da357642945e482d9ff355792910caef

Source dataset

uspto-grants-2005_04

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US06875771B2