Benzyl isocyanate → N-(6-Cyano-3,4-dihydro-2,2-dimethyl-2H-1-benzopyran-4-yl)-N'-(phenylmethyl)urea

Participants

Reaction Steps

A solution of the title D compound from Example 8 (0.50 g, 2.47 mmoles) and benzyl isocyanate (0.33 g, 2.47 mmoles) in anhydrous ethanol (4 ml) was heated at reflux for 3 hours and cooled to room temperature. The reaction product precipitated from solution. It was collected by suction filtration; the solid was triturated with diisopropyl ether and dried under vacuum to obtain 0.71 g of the title compound as a white solid, m.p. 168°-169° C. 1H NMR (DMSO-d6) δ7.59 (s, 1H), 7.56 (s, 1H), 7.38-7.24 (m, 5H) 6.89 (d, J=8.21 Hz, 1H), 6.56 (t, J=5.87 Hz, 1H), 6.50 (d, J=8.21 Hz, 1H), 4.94 (M, 1H), 4.30 (d, J=5.86 Hz, 2H), 2.10 (m, 1H), 1.74 (m, 1H), 1.41 (s, 3H), 1.28 (s, 3H). 13C NMR (DMSO-d6) δ158.11, 157.19, 140.78, 132.25, 132.08, 128.22, 126.93, 126.61, 126.12, 119.18, 118.03, 102.02, 77.28, 43.01, 41.95, 38.81, 29.08, 24.42.

Provenance & Evidence