Water → HCID 18533212, compound

HRID 413339Notes

Reaction equation

HRID 413339 reaction equation
Br[C:2]1[C:7]2[C:8](=[O:11])[NH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1.[Cu][C:13]#[N:14].O.[C-]#N.[Na+]>CN(C=O)C>[C:13]([C:2]1[C:7]2[C:8](=[O:11])[NH:9][O:10][C:6]=2[CH:5]=[CH:4][CH:3]=1)#[N:14]

Participants

6

Reactant 4

HCID 962WaterHCID 8929Sodium CyanideHCID 185332134-Bromo-1,2-benzoxazol-3(2H)-oneHCID 178418546HCID 178418546, compound

Product 1

HCID 18533212HCID 18533212, compoundYield 51.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
165 °C

Procedure

To a solution of 4-bromo-1,2-benzoxazolinone (5.0 g, 23 mmol) in DMF (11 mL) was added copper (I) cyanide (3.6 g, 39 mmol) and the reaction heated at 165° C. After 6.5 h, the reaction mixture was cooled to rt and water (20 mL) and sodium cyanide (3.6 g) were added and the reaction heated at 100° C. After 12 h, the reaction mixture was extracted with ethyl acetate and the combined organic layers were filtered through a scrub pad of silica gel eluting with ethyl acetate. The filtrate was concentrated under reduced pressure to give 1.9 g (51%) of 4-cyano-1,2-benzoxazolinone as a brown solid which required no further purification. 1H NMR (400 MHz, DMSO) δ 7.8 (s, 1H), 7.6 (d, 1H), 7.2 (d, 1H).

Workup

  1. temperaturethe reaction mixture was cooled to rt
  2. temperaturethe reaction heated at 100° C
  3. waitAfter 12 h
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. filtrationthe combined organic layers were filtered through a scrub pad of silica gel eluting with ethyl acetate
  6. concentrationThe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4f72dcc99ccf4a5ea662de4317230032
Source dataset
uspto-grants-2003_05
Patent number
US06566387B1

Reaction notes

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