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

HRID 1351335Notes

Reaction equation

HRID 1351335 reaction equation
[CH2:1]([N:3]=[C:4]=[O:5])[CH3:2].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[C:8](=[O:15])[NH:7]1>C1COCC1>[CH2:1]([NH:3][C:4]([N:7]1[C:8](=[O:15])[C:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=2[O:6]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 8022Ethyl isocyanateHCID 2108303-Hydroxy-1,2-benzisoxazole

Product 1

HCID 112642143-Oxo-3H-benzo[d]isoxazole-2-carboxylic acid ethylamideYield 75%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

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.

Workup

  1. concentrationAfter concentration and subsequent flash chromatography on silica (15% hexane in CH2Cl2)

Sources & evidence

ORD record
ord-6065f203ebae4e18a0befa162a9d6c72
Source dataset
uspto-grants-2007_05
Patent number
US07217727B2

Reaction notes

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