Methyl iodide → 7-Allyl-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-one

HRID 494950Notes

Reaction equation

HRID 494950 reaction equation
[CH2:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]2[CH2:12][O:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1)[CH:2]=[CH2:3].[H-].[Na+].I[CH3:20]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:4]1[C:5]([O:15][CH3:16])=[CH:6][C:7]2[CH2:12][O:11][C:10](=[O:13])[N:9]([CH3:20])[C:8]=2[CH:14]=1)[CH:2]=[CH2:3]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 576828047-Allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one

Product 1

HCID 576828547-Allyl-6-methoxy-1-methyl-1,4-dihydrobenz[d][1,3]oxazin-2-oneYield 92.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

210 mg of 7-allyl-6-methoxy-1,4-dihydrobenz[d][1,3]oxazin-2-one was dissolved in 6 ml of N,N-dimethylformamide. Thereafter, 46 mg of 60% sodium hydride was added to the reaction solution while cooling on ice. The obtained mixture was then stirred at room temperature for 20 minutes. Thereafter, while cooling on ice, 0.20 g of iodomethane was added to the reaction solution. The obtained mixture was then stirred at room temperature for 2 hours. Thereafter, the reaction solution was diluted with ethyl acetate and then washed with water and a saturated sodium chloride aqueous solution. The organic layer was dried over magnesium sulfate and then concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane-ethyl acetate), so as to obtain 207 mg of the subject compound.

Workup

  1. temperaturewhile cooling on ice
  2. additionwas added to the reaction solution
  3. stirringThe obtained mixture was then stirred at room temperature for 2 hours
  4. washwashed with water
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. concentrationconcentrated under a reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane-ethyl acetate)

Sources & evidence

ORD record
ord-f6451b2e86924755a5fa9105238fa55b
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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