1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 2-(Cyclopropylamino)-5,6-dichloro-1H-benzimidazole

Participants

Reaction Steps

4,5-Dichloro-1,2-phenylenediamine (6.04 g, 34.1 mmol), cyclopropyl isothiocyanate (3.69 g, 37.2 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (20.1 g, 47.4 mmol) and pyridine (135 mL) were used according to general procedure I. The product was recrystallized from acetonitrile to afford 5.82 g (70%) of a yellow solid; m.p. 223-225° C. 1H NMR (DMSO-d6) δ: 11.2 (s, 1H, NH), 7.43 (s, 1H, NH), 7.27 (s, 2H, ArH), 2.49 (m, 1H, CH), 0.70 (m, 2H, CH), 0.49 (m, 2H, CH).

Provenance & Evidence