Sodium hydride → HCID 86638508, compound

Participants

Reaction Steps

In a 250-mL round-bottom flask, a mixture of 1-{4-[(Z)-1-(trifluoromethyl)-2-(4-{[1-(trifluoromethyl)cyclopropyl]methyl}-1H-imidazol-2-yl)vinyl]phenyl}-1H-pyrazole (5.05 g, 11.8 mmol) and 60 wt % sodium hydride (0.89 g, 22 mmol) were mixed with tetrahydrofuran (80 mL). After bubbling ceased, dimethylsulfamoyl chloride (2.6 mL, 24.26 mmol) was added, and the reaction mixture was stirred overnight. The reaction mixture was quenched with water and extracted with diethyl ether. The combined organic extracts were washed with brine, dried (potassium carbonate), and concentrated in vacuo to afford an orange solid. Chromatography over silica eluting with 25-40% ethyl acetate/hexanes afforded N,N-dimethyl-4-{[1-(trifluoromethyl)cyclopropyl]methyl}-2-{(1Z)-3,3,3-trifluoro-2-[4-(1H-pyrazol-1-yl)phenyl]prop-1-en-1-yl}-1H-imidazole-1-sulfonamide, as a yellow solid.

Provenance & Evidence