Allyl isocyanate → N-(2-Cyanophenyl)-N'-prop-2-en-1-ylurea

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Reaction Steps

A mixture of anthranilonitrile (10.0 g, 85 mmol) and allyl isocyanate (7.5 mL, 85 mmol) was slightly heated to dissolve. The resulting solution was allowed to stir at room temperature for two days. The solid was collected by filtration and washed with ether (10 mL) to give 14.4 g (100%) of 2-(3-allylureido)benzonitrile. An analytical sample was recrystallized from ethanol. IR (KBr): 3331, 3263, 2226 (CN), 1639 cm-1. 1H NMR (300 MHz, DMSO-d6): δ3.74 (p, 2H, CH2), 5.09 (q, 1H, =CH), 5.17 (q, 1H, =CH), 5.86 (m, 1H, CH), 7.09 (t, 2H, Ar--H), 7.56 (t, 1H, Ar--H), 7.67 (d, 1H, Ar--H), 8.43 (d, 1H, Ar--H), 7.65 (d, 1H, NH), 8.54 (s, 1H, NH). 13C NMR (75 MHz, DMSO-d6): δ41.47, 101.00, 114.97, 116.99, 120.61, 120.73, 122.22, 132.96, 133.83, 135.69, 142.66, 154.32. Anal. Calcd for C11H11N30 (201.23): C, 65.66; H, 5.51; N, 20.89. Found: C, 65.38; H, 5.51; N, 21.05.

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