Water → HCID 83762656, compound

HRID 2209284Notes

Reaction equation

HRID 2209284 reaction equation
[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]([CH3:12])([CH3:11])[C:8](=[O:10])[NH:9][C:4]=2[CH:3]=1.[H-].[Na+].I[CH3:18].O>CN(C=O)C.[Cl-].[Na+].O.CCOC(C)=O>[Br:1][C:2]1[CH:14]=[CH:13][C:5]2[O:6][C:7]([CH3:11])([CH3:12])[C:8](=[O:10])[N:9]([CH3:18])[C:4]=2[CH:3]=1

Participants

8

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 578292256-bromo-2,2-dimethyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 83762656HCID 83762656, compoundYield 67.7%

Reagents, catalysts & solvents 3

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

To a solution of 6-bromo-2,2-dimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one (185 mg, 0.722 mmol) in DMF (3 mL) at 0° C. was added NaH (43.3 mg, 1.08 mmol, 60%), and the reaction was stirred for 5 minutes. Iodomethane (205 mg, 1.45 mmol) was added the reaction was stirred at room temperature for 60 minutes. Water, EtOAc, and brine were added, the layers were separated and the organic layer was washed with brine. The organics were dried over MgSO4, filtered and concentrated. The residue was purified by flash chromatography (10-35% EtOAc in hexanes) to afford 6-bromo-2,2,4-trimethyl-2H-benzo[b][1,4]oxazin-3(4H)-one 7.31 (132 mg). LCMS-ESI+ (m/z): [M+H]+ calcd for C11H13BrNO2: 270.0; found: 270.0.

Workup

  1. stirringwas stirred at room temperature for 60 minutes
  2. customthe layers were separated
  3. washthe organic layer was washed with brine
  4. dry with materialThe organics were dried over MgSO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe residue was purified by flash chromatography (10-35% EtOAc in hexanes)

Sources & evidence

ORD record
ord-1ba25dbff3234d80a30ec377cbb14397
Source dataset
uspto-grants-2016_06
Patent number
US09376441B2

Reaction notes

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