Pyrazole → N,N-dimethyl-1H-pyrazole-1-sulfonamide

To a solution of pyrazole (10.0 g, 147 mmol) in dichloromethane (150 mL), triethylamine (26.6 mL, 192 mmol) and N,N-dimethylsulfamoyl chloride (20.0 mL, 181 mmol) were added and the reaction mixture was heated to reflux for approximately 60 h. The reaction mixture was then cooled to ambient temperature and filtered through a pad of silica gel using dichloromethane as an eluent. The filtrate was then concentrated under reduced pressure and treated with diethyl ether (100 mL) resulting in the formation of a solid. The suspension was filtered, and the precipitate was washed with diethyl ether. The combined filtrates were combined and concentrated in vacuo to give 27.46 g of the title compound. This compound was of sufficient purity to use in subsequent reactions. 1H NMR (CDCl3) δ 2.94 (s, 6H), 6.40 (s, 1H), 7.75 (s, 1H), 7.99 (s, 1H).

1. temperaturethe reaction mixture was heated
2. temperatureto reflux for approximately 60 h
3. filtrationfiltered through a pad of silica gel
4. concentrationThe filtrate was then concentrated under reduced pressure
5. additiontreated with diethyl ether (100 mL)
6. customresulting in the formation of a solid
7. filtrationThe suspension was filtered
8. washthe precipitate was washed with diethyl ether
9. concentrationconcentrated in vacuo

ORD record

ord-f054036dbc824d19aada5db41c4f904c

Source dataset

uspto-grants-2013_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08586611B2