4-Methylpyrazole → HCID 90029806, compound

Temperature

0 °C

Into a 500-mL round-bottom flask purged and maintained with an inert atmosphere of nitrogen, was placed a solution of 4-methyl-1H-pyrazole (10.4 g, 127.2 mmol) in CH2Cl2 (200 mL). N,N-dimethylsulfamoyl chloride (17.14 mL, 167.1 mmol) and triethylamine (35 mL, 251.1 mmol) were added to the reaction. The reaction mixture was stirred for 30 min at 0° C. in a water/ice bath and then stirred overnight at room temperature. The reaction was quenched with NaHCO3 (sat.) (40 mL) and the aqueous phase was extracted with 3×200 mL of EtOAc. The combined organic phase was dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was purified by silica gel chromatography with ethyl acetate/hexanes (1:6) as the eluent to afford the title compound (22.2 g, 92%) as a light yellow oil.

1. customInto a 500-mL round-bottom flask purged
2. temperaturemaintained with an inert atmosphere of nitrogen
3. stirringstirred overnight at room temperature
4. customThe reaction was quenched with NaHCO3 (sat.) (40 mL)
5. extractionthe aqueous phase was extracted with 3×200 mL of EtOAc
6. dry with materialThe combined organic phase was dried over anhydrous sodium sulfate
7. concentrationconcentrated under reduced pressure
8. customThe residue was purified by silica gel chromatography with ethyl acetate/hexanes (1:6) as the eluent

ORD record

ord-6e69abc61490428eb12a52852083837e

Source dataset

uspto-grants-2016_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US09428502B2