Methyl 4-(bromomethyl)benzoate → HCID 667702, compound

Participants

Reaction Steps

1H-Benzoimidazol-2-thiol (1.5 g, 0.01 mol) and 4-bromomethyl benzoic acid methyl ester (2.29 g; 0.01 mol) were heated at reflux in methanol (100 mL) for a period of 24 hours. The solvent was evaporated. The residue was dissolved in ethyl acetate and washed with saturated sodium bicarbonate solution, then with water. The organic phase was evaporated. The residue was dissolved in methanol. The resulting solution was saturated with hydrogen chloride. The solution was then concentrated to the precipitation point. The solid was collected and dried to give (1.8 g, 54% yield) of the title compound as a mono-hydrochloride, white solid, m.p. 229°-231° C. Anal. Calcd. for C16H14N2 O2S.HCl: C, 57.40; H, 4.52; N, 8.37. Found: C, 57.54; H, 4.47; N, 8.36. Mass spectrum (EI; M+) m/z 298. 1H-NMR (DMSO-d6 ; 400 MHz) δ 7.89 (d, 2H0, 7.62-7.65 (m, 4H); 7.39 (m, 2H), 4.89 (s, 2H), and 3.81 (s, 3H).

Provenance & Evidence