Ethyl Acetate → HCID 53688815, compound

Participants

Reaction Steps

A solution of 1-[(2-benzimidazolyl)thiocarbamoyl]imidazole (1.22 g, 5.0 mmol) and 2-(4-chlorophenyl)ethylamine (0.79 g, 5.0 mmol) in N,N-dimethylformamide (20 mL) was stirred at 90° C. for 2 h. The reaction was cooled to room temperature, poured into ethyl acetate, washed with water, 1N aqueous HCl, water, saturated sodium bicarbonate, and brine. The organic layer was concentrated and the resultant solid was crystallized from EtOAc to provide 1.31 g (79%) of the titled product as a white solid: mp 173°-182° C.; IR (KBr, cm-1) 3168, 3031, 1668, 1562, 1494, 1470, 1327, 1221, 1174, 1090, 817, 777, 742, 657, 526, 457; 1H NMR (300 MHz, DMSO-d6) δ 12.18 (br s, 1H), 10.36 (br s, 1H), 7.52 (m, 2H), 7.22-7.38 (m, 7H), 3.76 (m, 2H), 2.89 (t, J=7 Hz, 2H); MS (FD) m/e 330 (M+), 332 (M+2); UV (EtOH) 301 nm (ε=21672), 293 nm (ε=22296), 266 nm (ε=13408), 260 nm (ε=12591), 206 nm (ε=29310).

Provenance & Evidence