Sodium Cyanide → 2-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrile

HRID 590379Notes

Reaction equation

HRID 590379 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.[Cu][C:13]#[N:14].[C-]#N.[Na+]>CN(C=O)C.O>[O:9]=[C:7]1[NH:6][C:5]2[CH:10]=[CH:11][C:2]([C:13]#[N:14])=[CH:3][C:4]=2[O:8]1

Participants

6

Reactant 3

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

Product 1

HCID 101762552-Oxo-2,3-dihydro-1,3-benzoxazole-6-carbonitrileYield 100.3%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
150 °C

Procedure

A mixture of 6-bromo-1,3-benzoxazol-2(3H)-one (2 g; 9.34 mmol) and copper (I) cyanide (1.42 g; 15.86 mmol) in 6 ml DMF is heated at 150° C. under nitrogen atmosphere for 22 hr. After cooling to room temperature, a solution of 1.55 g (31.6 mmol) of sodium cyanide in 32 ml water is added followed by 1 hr stirring. The system is extracted thoroughly with ethyl acetate, washed with brine, dried and concentrated in vacuo to provide 1.5 g (93% yield) of the title compound enough pure as to prosecute the synthesis.

Workup

  1. temperatureAfter cooling to room temperature
  2. extractionThe system is extracted thoroughly with ethyl acetate
  3. washwashed with brine
  4. customdried
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-24f92b951ba74a4e966ce4e5dc6ba227
Source dataset
uspto-grants-2016_01
Patent number
US09233108B2

Reaction notes

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