1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 4,6-Dichloro-N-(propan-2-yl)-1H-benzimidazol-2-amine

Participants

Reaction Steps

3,5-Dichloro-1,2-phenylenediamine (1.30 g, 7.32 mmol), isopropyl isothiocyanate (0.81 g, 8.00 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (4.19 g, 9.89 mmol) and pyridine (25 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 1.07 g (60%) of a white solid; 1H NMR (DMSO-d6) δ: 10.9 (s, 1H, NH), 7.07 (d, J=1.5 Hz, 1H, ArH), 6.98 (d, J=1.6 Hz, 1H, ArH), 6.92 (d, J=7.9 Hz, 1H, NH), 3.89 (m, 1H, CH), 1.17 (d, J=6.6 Hz, 6H, overlapping CH3).

Provenance & Evidence