6-Bromo-2(3H)-benzoxazolone → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

HRID 1846204Notes

Reaction equation

HRID 1846204 reaction equation
Br[C:2]1[CH:11]=[CH:10][C:5]2[NH:6][C:7](=[O:9])[O:8][C:4]=2[CH:3]=1.[C:12]([Cu])#[N:13]>CN(C=O)C.CCOC(C)=O>[O:9]=[C:7]1[NH:6][C:5]2[CH:10]=[CH:11][C:2]([C:12]#[N:13])=[CH:3][C:4]=2[O:8]1

Participants

5

Reactant 2

HCID 298596-Bromo-2(3H)-benzoxazoloneHCID 178418546HCID 178418546, compound

Product 1

HCID 101762552-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent2×

Conditions

Temperature
175 °C

Procedure

To a solution of 6-bromo benzoxazolinone (2 g, 9.4 mmol) in DMF (20 mL) was added CuCN (16.79 g, 188 mmol), and the reaction was stirred at 175° C. for 6 h. The reaction progress was monitored by TLC (100% EtOAc). The reaction was diluted with EtOAc (10 mL) and filtered through Celite® brand filter agent. The organic layer was concentrated and purified by column chromatography (silica gel, 0-50% EtOAc in hexanes) to give the title compound. MS (ESI pos. ion) m/z: 158.9 (MH−).

Workup

  1. filtrationfiltered through Celite® brand
  2. filtrationfilter agent
  3. concentrationThe organic layer was concentrated
  4. custompurified by column chromatography (silica gel, 0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-cbfb010c97c54416a2a4687603727953
Source dataset
uspto-grants-2015_02
Patent number
US08952009B2

Reaction notes

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