Tetrahydrofuran → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

HRID 1533167Notes

Reaction equation

HRID 1533167 reaction equation
N[C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1O)[C:5]#[N:6].[C:11]([N:18]1C=CN=C1)(N1C=CN=C1)=[O:12].C1C[O:26]CC1>>[C:5]([C:4]1[CH:7]=[CH:8][C:9]2[NH:18][C:11](=[O:12])[O:26][C:2]=2[CH:3]=1)#[N:6]

Participants

4

Reactant 3

HCID 8028TetrahydrofuranHCID 682631,1'-CarbonyldiimidazoleHCID 2712583-Amino-4-hydroxybenzonitrile

Product 1

HCID 101762552-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrileYield 100%

Procedure

To a solution of 3-amino-4-hydroxybenzonitrile (8.2 g, 61 mmol) in THF (200 mL) was added 1,1′-carbonyldiimidazole (11.6 g, 72 mmol) and the resulting mixture was stirred at room temperature for 16 hours. The reaction was then quenched with 1N HCl (50 mL), and the mixture was extracted with EtOAc (200 mL). The organic layer was washed with brine, dried over MgSO4, and concentrated to give 6-cyanobenzoxazolinone (9.8 g, 100%). 1H NMR (CDCl3) δ 7.49 (dd, J=8.4 Hz, J=1.5 Hz, 1H), 7.34 (d, J=1.5 Hz, 1H), 7.31 (d, J=8.4 Hz, 1H), 7.15 (d, J=0.9 Hz, 1H).

Workup

  1. customThe reaction was then quenched with 1N HCl (50 mL)
  2. extractionthe mixture was extracted with EtOAc (200 mL)
  3. washThe organic layer was washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6ac978cd630042e68e8fa6dcc4ef8c04
Source dataset
uspto-grants-2001_03
Patent number
US06207697B1

Reaction notes

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