Phenyl isocyanate → HCID 10091155, compound

Participants

Reaction Steps

A suspension of (trans)-4-amino-3,4-dihydro-3-hydroxy-2,2-dimethyl-6-trifluoromethyl-2H-1-benzopyran (0.5 g, 1.9 mmol) (prepared according to D. R. Buckle et al., J. Med. Chem., 1990, 33, p. 3028) in ethanol (5 ml) under argon was treated with phenylisocyanate (0.23 g, 1.9 mmol) and the reaction was heated at reflux temperature for 4 hours. The product precipitated out of the reaction. The reaction was then concentrated in vacuo and the residue was triturated with isopropyl ether and hexanes to give the title compound as a colorless solid (0.5 g), m.p. 174-175° C.: 1H NMR (CDCl3) δ 7.4 (s, 1 H), 7.32 (d, J=9.8 Hz, 1 H), 7.17 (m, 5 H), 7.0 (m, 1 H), 6.77 (d, J=8.2 Hz, 1 H), 5.22 (br d, 1H), 4.80 (br t, 1 H), 3.45 (d, J=9.4 Hz, 1 H), 1.37 (s, 3 H), 1.12 (s, 3 H); 13C NMR (CDCl3) 157.0, 156.5, 139.1, 137.3, 129.4, 126.5, 125.0, 124.7, 122.0, 121.7, 118.0, 79.6, 76.4, 51.4, 26.3, 18.2; IR (KBr) 1118.5, 1264.8, 1332.1, 1443.4, 1500.9, 1558.3, 1598.8, 1647.8, 2981.4, 3391.3 cm-1.

Provenance & Evidence