Ethyl isocyanate → 3-Oxo-3H-benzo[d]isoxazole-2-carboxylic acid ethylamide

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Reaction Steps

Ethyl isocyanate (92.4 mg, 1.30 mmol) is added to a stirred solution of benzo[d]isoxazol-3-one (150 mg; 1.10 mmol) in anhydrous THF (4 mL) at ambient temperature under nitrogen. The resultant mixture is heated in an oil bath at 70° C. for 2 hr. After concentration and subsequent flash chromatography on silica (15% hexane in CH2Cl2), 6-1 is obtained as a white solid (170 mg, 75% yield). mp 112.0–113.0° C.; 1H-NMR (CDCl3) δ1.28 (t, J=7.3 Hz, 3H), 3.43–3.51 (m, 2H), 7.21–7.29 (m, 3H), 8.04 (br s, 1H), 8.07 (d, J=6.8 Hz, 1H); ESIMS m/e 207 (M+H)+. Analysis for C10H10N2O3: calcd: C, 58.25; H, 4.89; N, 13.59; found: C, 58.04; H, 4.82; N, 13.41.

Provenance & Evidence