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

Temperature

50 °C

To an acetonitrile (500 mL) solution of 1H-imidazole-2-carboaldehyde (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. After the reaction solution was cooled to room temperature, the precipitated crystal was removed by filtration and the filtrate was concentrated under reduced pressure. The residue was washed with ethyl acetate to obtain the crude title compound. The washing was washed with saturated brine 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 the crude title compound. The obtained compound was combined with the crystal obtained previously and then washed with ether to obtain the title compound (88.32 g) having the following physical properties.

1. temperatureAfter the 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 the crude title compound
6. washThe washing was washed with saturated brine
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 the crude title compound
13. customobtained previously
14. washwashed with ether

ORD record

ord-3ebfcadbdbd743188d9536edb5bf0bd3

Source dataset

uspto-grants-2013_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08519124B2