Benzyl isocyanate → HCID 15291499, compound

Participants

Reaction Steps

A solution of 3-amino-5-cyano-1,1-dimethylindane (0.40 g, 2.15 mmol, prepared according to part F of Example 6) and benzyl isocyanate (0.29 g, 2.15 mmole) in ethanol (3.5 ml) under argon was heated at reflux for three hours. The solvent was recovered under vacuum to obtain 0.87 g of yellow gum. The crude product was chromatographed on silica eluting with 1:1 ethyl acetate/hexane to obtain an amorphous white solid (0.44 g). The chromatogrpahy isolate was further purified by crystallization from isopropyl ether to afford the title compound as a pure white solid (0.40 g), m.p. 130°-132° C. 1H NMR δ 7.71 (d, J=8.21 Hz, 1H), 7.52 (s, 1H), 7.44 (d, J=7.63 Hz, 1H), 7.31 (m, 5H), 6.44 (m, 2H), 5.22 (m, 1H), 4.28 (d, J=5.86, 2H), 2.30 (dd, J=7.04, 12.90 Hz, 1H), 1.71 (dd, J=9.38, 12.31 Hz, 1H), 1.35 (s, 3H), 1.17 (s, 3H); 13C NMR δ 157.97, 156.88, 145.38, 140.75, 131.88, 128.19, 127.59, 126.98, 126.58, 123.50, 119.06, 109.33, 52.06, 48.74, 42.98, 42.00, 28.64, 28.21.

Provenance & Evidence