Ethyl isocyanate → HCID 89650477, compound

Participants

Reaction Conditions

Reaction Steps

Ethyl isocyanate (0.898 mL, 1.49 mmol), was added to a solution of compound vi (0.270 g, 0.99 mmol) in 1,4-dioxane (5 mL). The reaction mixture was warmed to 100° C. for 48 h, cooled to room temperature and reduced in vacuo. The resulting orange residue was re-dissolved in EtOAc (15 mL) and reduced in vacuo on to SiO2. Column chromatography (SiO2), eluting with 2:1 Hexanes-EtOAc, gave the desired compound vii. (0.145 g, 0.424 mmol, 43%) as an off-white solid, 1H NMR (300 MHz, DMSO-d6): δ 9.62 (1H, br s), 9.19 (1H, br s), 8.62 (1H, s), 7.85 (1H, br t), 7.31 (1H, t, J 7.7), 7.23 (1H, s), 7.13-7.07 (2H, m), 7.03 (1H, d, J 7.2), 4.31 (2H, q, J 7.2), 3.13 (2H, dq, J 6.7 and 7.2), 2.33 (3H, s), 1.33 (3H, t, J 7.2), 1.05 (3H, t, J 7.2); [M+H]+ m/z=343.1.

Provenance & Evidence