Nitric Acid → HCID 9882022, compound

Participants

Reaction Conditions

Reaction Steps

To stirred concentrated sulfuric acid (11 mL) was added 1,1,1-trifluoro-2-benzimidazol-2-ylpropan-2-ol (3.00 g) under a nitrogen atmosphere while maintaining the temperature at 5° C. The reaction mixture was treated with a nitrating reagent (3.5 mL) containing concentrated nitric acid and concentrated sulfuric acid (1.5 mL), while maintaining the reaction temperature below 35° C., and was then stirred for 1 hour at ice bath temperature. The reaction mixture was then poured onto ice, neutralized to pH 7-8, extracted with diethyl ether, and dried. The solvent was evaporated to leave a gold oil. Trituration of the oil with diethyl ether provided the title compound as a white solid (0.80 g); mp 73°-75° C., resolidified mp 173°-174° C.; NMR (250 MHz): 1.68 (s,3), 7.62 (s,1), 7.78 (broad d,1), 8.19 (dd,1), 8.52 (s,1), 13.4 (s,1); MS: m/z=276 (M+1). Analysis for C10H8F3N3O: Calculated C, 43.65; H, 2.93; N, 15.27; Found: C, 43.32; H, 3.02; N, 15.03.

Provenance & Evidence