Sodium hydride → HCID 89544282, compound

HRID 2203450Notes

Reaction equation

HRID 2203450 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:11][C:10](=[O:12])[NH:9][C:8]=2[CH:13]=1.[CH:14](Br)([C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1)[C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1>CN(C)C=O>[CH:14]([N:9]1[C:8]2[CH:13]=[C:4]([Br:3])[CH:5]=[CH:6][C:7]=2[O:11][C:10]1=[O:12])([C:15]1[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1)[C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 268532-Benzoxazolinone, 5-bromo-HCID 236603Bromodiphenylmethane2×

Product 1

HCID 89544282HCID 89544282, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

To a cold (0° C.) suspension of sodium hydride (0.589 g of a 60% w/w dispersion in mineral oil, 14.7 mmol) in N,N-dimethylformamide (50 mL) was added in portions 5-bromo-benzo[d]oxazol-2(3H)-one (3.0 g, 14.0 mmol). The reaction mixture was stirred for 1 h at 0° C. and benzhydryl bromide (3.81 g, 15.4 mmol) was added. The reaction mixture was allowed to warm to ambient temperature and stirred for 16 h. Further benzhydryl bromide (1.7 g. 6.9 mmol) was added and the reaction mixture was heated at 70° C. for 16 h, allowed to cool to ambient temperature and concentrated in vacuo. The residue was suspended in ethyl acetate (300 mL), washed with water (2 20 mL) and brine (2 20 mL), dried over anhydrous sodium sulphate, filtered and concentrated in vacuo. The residue was purified by column chromatography, eluting with a 0-50% gradient of ethyl acetate in hexanes to afford 3-benzhydryl-5-bromobenzo[d]oxazol-2(3H)-one as an orange solid in 71% yield (3.87 g): 1H NMR (300 MHz, CDCl3) δ7.41-7.34 (m, 6H), 7.27-7.21 (m, 4H), 7.19-7.14 (m, 1H), 7.06 (d, J=8.5 Hz, 1H), 6.78 (s, 1H), 6.46 (s, 1H).

Workup

  1. temperatureto warm to ambient temperature
  2. stirringstirred for 16 h
  3. temperaturethe reaction mixture was heated at 70° C. for 16 h
  4. temperatureto cool to ambient temperature
  5. concentrationconcentrated in vacuo
  6. washwashed with water (2 20 mL) and brine (2 20 mL)
  7. dry with materialdried over anhydrous sodium sulphate
  8. filtrationfiltered
  9. concentrationconcentrated in vacuo
  10. customThe residue was purified by column chromatography
  11. washeluting with a 0-50% gradient of ethyl acetate in hexanes

Sources & evidence

ORD record
ord-f9b712385a62410ca72d59ec9fef04c1
Source dataset
uspto-grants-2016_06
Patent number
US09365578B2

Reaction notes

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