1-Cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate → HCID 18472118, compound

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Reaction Steps

5-Chloro-3,4difluoro-1,2-phenylenediamine (11.6 g, crude material), isopropyl isothiocyanate (6.3 g, 62.1 mmol), 1-cyclohexyl-3-(2-morpholinoethyl)carbodiimide metho-p-toluenesulfonate (28.0 g, 66.2 mmol) and pyridine (250 mL) were used according to general procedure I. The title compound was recrystallized from 1,4-dioxane to provide a tan solid (3.2 g, 25%); m.p. 175-178° C.; 1H NMR (DMSO-d6) δ: 11.0 (br s, 1H, NH), 7.07 (d, J=5.4 Hz, 1H, Ar—H), 6.96 (br s, 1H, NH), 3.93 (m, 1H, CH), 1.23 (d, J=6.5 Hz, 6H, overlapping CH3). Anal. Calcd. for C10H10F2ClN3-(0.6 C4H8O2): C, 49.89; H, 5.00; N, 14.08. Found: C, 50.29; H, 4.99; N, 14.47.

Provenance & Evidence