Benzimidazole → 1-Benzyl-1H-benzimidazole

Participants

Reaction Steps

To benzyl chloride (13 g, 0.103 mol), 1H-benzimidazole (11.81 g, 0.10 mol), K2CO3 (60 g, 0.434 mol) was added acetonitrile (200 mL) and the mixture was stirred and heated under reflux for 3 h, filtered hot, and washed with hot CH3CN (100 mL). The solvent of the filtrate was evaporated and the residual mass recrystallized as needles (16.5 g, 79%): mp 119°-120° C. (benzene) (lit1 mp 105° C.); 1H NMR (270 MHz, CDCl3) δ5.40 (s, 2H, CH2), 7.20-7.41 (m, 8H), 7.85-7.89 (m, 1H), 8.02 (s, 1H, NCHN); IR (CDCl3) 3093 (w), 3065 (w), 3037 (w), 2929 (w), 1615 (w), 1496 (s), 1456, 1385 (w), 1361, 1331, 1285, 1261, 1204, 1181, 1007 (w), 963 (w), 947 (w) cm1. MS (EI) m/e 208 (M+, 57.8), 91 (100); Anal. Calcd for C14H22N2 (208.26): C, 80.74; H, 5.81; N, 13.45; Found: C, 80.70; H, 6.02; N, 13.31.

Provenance & Evidence