1,1'-Carbonyldiimidazole → 2-Oxo-2,3-dihydro-benzooxazole-5-carbonitrile

HRID 552826Notes

Reaction equation

HRID 552826 reaction equation
[NH2:1][C:2]1[CH:3]=[C:4]([CH:7]=[CH:8][C:9]=1[OH:10])[C:5]#[N:6].C1N=CN([C:16](N2C=NC=C2)=[O:17])C=1>CN(C=O)C.O>[O:17]=[C:16]1[NH:1][C:2]2[CH:3]=[C:4]([C:5]#[N:6])[CH:7]=[CH:8][C:9]=2[O:10]1

Participants

5

Reactant 2

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

Product 1

HCID 129690942-Oxo-2,3-dihydro-benzooxazole-5-carbonitrileYield 74.2%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-amino-4-hydroxybenzonitrile (730 mg) in DMF (10 ml) was added CDI (1.06 g) at 0° C., followed by stirring at room temperature for 3.5 hours. The reaction solution was diluted with water (10 ml), and extracted with EtOAc (200 ml). The organic layer was dried over anhydrous MgSO4, and then filtered, and the filtrate was concentrated under reduced pressure. The residue was purified by silica gel column chromatography (chloroform:CH3OH=98:2 to 93:7) to obtain 2-oxo-2,3-dihydro-1,3-benzoxazole-5-carbonitrile (647 mg) as a pale yellow solid.

Workup

  1. extractionextracted with EtOAc (200 ml)
  2. dry with materialThe organic layer was dried over anhydrous MgSO4
  3. filtrationfiltered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (chloroform:CH3OH=98:2 to 93:7)

Sources & evidence

ORD record
ord-5cd956fca9f84e4dbd755ecf4a20ee01
Source dataset
uspto-grants-2011_05
Patent number
US07951825B2

Reaction notes

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