Methyl Isocyanate → HCID 24821414, compound

Participants

Reaction Steps

To a solution of Example 4D (0.32 g, 0.0009 mol) in methylene chloride (15 mL) was added excess methyl isocyanate (0.25 mL) and the mixture was stirred at room temperature for 0.5 hours. After quenching with methanol (10 mL), the solvent was concentrated and the residue was purified on silica gel (75˜100% ethyl acetate in hexane) to give 0.28 g of the title compound (76% yield). 1H NMR (300 MHz, DMSO-d6) 5 ppm 1.29 (d, J=6.25 Hz, 6 H) 1.34 (d, J=6.99 Hz, 3 H) 2.51 (d, J=4.78 Hz, 3 H) 4.55-4.70 (m, 1 H) 4.71-4.85 (m, 1 H) 5.72 (q, J=4.41 Hz, 1 H) 6.48 (d, J=8.09 Hz, 1 H) 6.96-7.07 (m, 2 H) 7.28-7.39 (m, 2 H) 7.77-7.81 (m, 1 H) 7.83 (s, 1 H) 8.42 (d, J=1.84 Hz, 1 H) 8.67 (d, J=2.21 Hz, 1 H). MS (ESI), m/z 413.1 (M+1)+.

Provenance & Evidence