Water → Cyclohexanesulfonamide

To a suspension of cyclohexanesulfonic acid sodium salt (2.5 g) in DMF (15 mL) was added thionyl chloride (1.96 mL) under ice-cooling, and the mixture was stirred at room temperature for 29 hr. The reaction mixture was added to a mixture of ice-cooled water (100 mL) and toluene (100 mL), and the mixture was extracted. The organic layer was concentrated under reduced pressure. THF (50 mL) was added to the residue, 28% aqueous ammonia (10 mL) was added dropwise to the solution under ice-cooling, and the mixture was stirred at room temperature for 17 hr. After concentration under reduced pressure, water (100 mL) and ethyl acetate (100 mL) were added to extract the residue. The organic layer was concentrated under reduced pressure to give the title compound (760 mg) as a white solid.

1. temperaturecooling
2. additionThe reaction mixture was added to a mixture of ice-
3. extractionthe mixture was extracted
4. concentrationThe organic layer was concentrated under reduced pressure
5. additionTHF (50 mL) was added to the residue, 28% aqueous ammonia (10 mL)
6. additionwas added dropwise to the solution under ice-
7. temperaturecooling
8. stirringthe mixture was stirred at room temperature for 17 hr
9. concentrationAfter concentration under reduced pressure, water (100 mL) and ethyl acetate (100 mL)
10. additionwere added
11. extractionto extract the residue
12. concentrationThe organic layer was concentrated under reduced pressure

ORD record

ord-8d6334aad5634cc09bde166510d0dff9

Source dataset

uspto-grants-2013_06

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08461209B2