Dimethylformamide → 2,3-Dihydro-4-hydroxy-2-oxo-6-benzoxazolecarbonitrile

HRID 842334Notes

Reaction equation

HRID 842334 reaction equation
CN(C=[O:5])C.Br[C:7]1[CH:16]=[CH:15][C:10]2[NH:11][C:12](=[O:14])[O:13][C:9]=2[CH:8]=1.[C:17]([Cu])#[N:18].[C-]#N.[Na+]>O>[OH:5][C:15]1[C:10]2[NH:11][C:12](=[O:14])[O:13][C:9]=2[CH:8]=[C:7]([C:17]#[N:18])[CH:16]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 8929Sodium CyanideHCID 298596-Bromo-2(3H)-benzoxazoloneHCID 178418546HCID 178418546, compound

Product 1

HCID 112867672,3-Dihydro-4-hydroxy-2-oxo-6-benzoxazolecarbonitrileYield 88.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
150 °C

Procedure

To a solution of DMF (110 ml) was added 6-bromo-2(3H)-benzoxazolone (50 g, 0.234 mole) and CuCN (89.6 g, 0.398 mole) and the mixture heated to 150° C. for 6 h under nitrogen. The reaction was then cooled to 100° C., H2O (200 ml) and NaCN (36 g, 0.734 mole) added, the suspension stirred for 2 h at ambient temperature and partitioned with EtOAc at 70° C. The organic phase was washed with H2O (2×150 ml) and concentrated in vacuo to give the title compound as a tan solid (33.2 g, 88.5%); mp>220° C.; 1H NMR (DMSO-d6) δ 7.8 (s, 1 H), 7.6 (d, J=8.0 Hz, 1 H), 7.2 (d, J=8.0 Hz, 1 H).

Workup

  1. temperatureThe reaction was then cooled to 100° C.
  2. custompartitioned with EtOAc at 70° C
  3. washThe organic phase was washed with H2O (2×150 ml)
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-baf3a053b45b4378998d9ec0d00728cb
Source dataset
uspto-grants-2002_04
Patent number
US06372933B1

Reaction notes

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