1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → 4,5-Dichloro-N-(1-methylethyl)-1H-benzimidazol-2-amine

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Reaction Steps

3,4-Dichloro-1,2-phenylenediamine (8.00 g, 45.19 mmol), isopropyl isothiocyanate (5.26 g, 51.99 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (25.0, 59.02 mmol), and pyridine (250 mL) were used according to general procedure I. The product was recrystallized from 1,4-dioxane to afford 6.12 g (55%) of a white solid. MS (EI): m/z 244 (M+H); 1H NMR (DMSO-d6) δ: 11.08 (s, 1H, NH), 7.07 (d, J=8.3Hz, 1H, ArH), 7.00 (brs, 1H, NH), 6.99 (d, J=8.3Hz, 1H, ArH), 3.91 (m, 1H, CH), 1.21 (d, J=6.5 Hz, 6H, overlapping CH3).

Provenance & Evidence