5,6-Dimethyl-2-trifluoromethylbenzimidazole → HCID 15376227, compound

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Reaction Steps

5,6-Dimethyl-2-trifluoromethyl-1H-benzoimidazole (2.14 g, 0.01 mol) was dissolved in DMF (50 mL). Sodium hydride (60% dispersion in oil, 0.48 g, 0.012 mol) was added and the reaction mixture was stirred at ambient temperature for 0.5 hour under an atmosphere of nitrogen. 4-Bromomethyl benzoic acid methyl ester (2.29 g, 0.01 mol) was then added. The mixture was stirred at 80° C. for 18 hours. Most of the solvent was evaporated. The residue was diluted with water and extracted with ethyl acetate. The organic phase was washed with water, dried over anhydrous sodium sulfate then evaporated. The residue was crystallized from ethyl acetate/hexane twice to afford pure title compound (0.85 g, 23.5% yield) as a white solid, m.p. 150°-152° C. Anal. Calcd. for C19H17F3N2O2 : C, 62.98; H, 4.73; N, 7.73. Found: C, 62.96; H, 4.73; N, 7.56. Mass spectrum (+FAB; [M+H]+) 363. 1H-NMR (DMSO-d6; 400 MHz) δ 7.90 (d, 1H), 7.63 (s, 1H), 7.45 (s, 1H), 7.15 (d, 2H), 5.74 (2H), 3.81 (s, 3H), 2.33 (s, 3H), and 2.30 ppm (s, 3H).

Provenance & Evidence