Benzoyl isocyanate → N-(2-cyano-3-(2-methylprop-1-enyl)phenylcarbamoyl)benzamide

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Reaction Steps

Benzoyl isocyanate (88.1 mg, 0.60 mmol) was added to a solution of 2-amino-6-(2-methylprop-1-enyl)benzonitrile (Example 129b) (75.2 mg, 0.44 mmol) in anhydrous 1,4-dioxane under nitrogen, and was stirred at room temperature for 12 h. The mixture was concentrated under vacuum, and purified by chromatography on silica gel eluting with solvent gradient 0% to 15% MeOH in CH2Cl2, to give 125.0 mg (86%) of N-(2-cyano-3-(2-methylprop-1-enyl)phenylcarbamoyl)benzamide as a white solid. 1H NMR (400 MHz, DMSO-d6) δ 1.80 (d, J=1.2 Hz, 3H), 1.95 (d, J=1.2 Hz, 3H), 6.40 (s, 1H), 7.19 (m, 1H), 7.55 (m, 2H), 7.67 (m, 2H), 8.03 (m, 2H), 8.13 (m, 1H), 11.33 (s, 1H), 11.48 (s, 1H).

Provenance & Evidence