Phenyl isocyanate → HCID 9819354, compound

Participants

Reaction Steps

To a solution of trans-3-amino-1,1-dimethyl-2-hydroxy-5-nitro indane (0.75 g, 3.37 mmoles, as prepared in part H of Example 1) in refluxing ethanol (6 ml) was added phenyl isocyanate (0.40 g, 3.37 mmoles). The reaction mixture was heated at reflux for 3 hours and cooled to room temperature. The product, which had precipitated from solution, was collected via suction filtration and washed with isopropyl ether. In this manner 0.82 g of the title compound was obtained as a white solid, m.p. 194°-195° C. 1H NMR (DMSO-d6) δ 8.66 (s, 1H), 8.16 (d, J=8.79 Hz, 1H), 7.94 (s, 1H), 7.51 (m, 3H), 7.28 (m, 2H), 6.95 (m, 1H), 6.73 (d, J=7.62 Hz, 1H), 5.67 (d, J=5.28 Hz, 1H), 5.00 (t, J=8.21 Hz, 1H), 3.86 (dd, J=5.86 and 8.79 Hz, 1H), 1.36 (s, 3H), 1.09 (s, 3H). 13C NMR (DMSO-d6) δ 156.53, 155.75, 146.91, 142.36, 140.26, 128.74, 123.96, 123.47, 121.37, 118.63, 117.91, 84.71, 57.70, 44.11, 25.07, 22.42.

Provenance & Evidence