Acetonitrile → 2-formyl-N,N-dimethyl-1H-imidazole-1-sulfonamide

Temperature

50 °C

To an acetonitrile (500 mL) solution of 2-formylimidazole (64 g) and triethylamine (140 mL), dimethylsulfamoyl chloride (100 g) was added at room temperature. The reaction solution was stirred at 50° C. for 16 hours. The reaction solution was cooled to room temperature and the precipitated crystal was removed by filtration, and then the filtrate was concentrated under reduced pressure. The residue was washed with ethyl acetate to obtain a crude compound. The wash solution was washed with saturated sodium chloride solution and then dried over anhydrous sodium sulfate. After removing the anhydrous sodium sulfate by filtration, the filtrate was concentrated. The residue was purified by silica gel chromatography (ethyl acetate) to obtain a crude product. The crude product was combined with the crude product obtained previously, followed by washing with ether to obtain the title compound (88.3 g) having the following physical properties.

1. temperatureThe reaction solution was cooled to room temperature
2. customthe precipitated crystal was removed by filtration
3. concentrationthe filtrate was concentrated under reduced pressure
4. washThe residue was washed with ethyl acetate
5. customto obtain a crude compound
6. washThe wash solution was washed with saturated sodium chloride solution
7. dry with materialdried over anhydrous sodium sulfate
8. customAfter removing the anhydrous sodium sulfate
9. filtrationby filtration
10. concentrationthe filtrate was concentrated
11. customThe residue was purified by silica gel chromatography (ethyl acetate)
12. customto obtain a crude product
13. customobtained previously
14. washby washing with ether

ORD record

ord-5be318e6c18f4e64b58285e343ed1bd0

Source dataset

uspto-grants-2012_11

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08318931B2