Methyl iodide → HCID 57682832, compound

HRID 494931Notes

Reaction equation

HRID 494931 reaction equation
[CH3:1][O:2][C:3]1[C:14]([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:13][C:6]2[C:7](=[O:12])[NH:8][CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1.[H-].[Na+].[CH3:22]I.[Cl-].[NH4+]>CN(C)C=O.C(OCC)(=O)C>[CH3:1][O:2][C:3]1[C:14]([CH2:15][CH:16]=[C:17]([CH3:19])[CH3:18])=[CH:13][C:6]2[C:7](=[O:12])[N:8]([CH3:22])[CH2:9][CH2:10][O:11][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 25517Ammonium ChlorideHCID 57682783HCID 57682783, compound

Product 1

HCID 57682832HCID 57682832, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

601 mg of 8-methoxy-7-(3-methyl-2-butenyl)-3,4-dihydro-2H-benz[f][1,4]oxazepin-5-one was dissolved in 15 ml of N,N-dimethylformamide. Thereafter, 120 mg of sodium hydride was added to the reaction solution. Ten minutes later, 215 μl of methyl iodide was added to the reaction solution, and the obtained mixture was then stirred at room temperature. After completion of the reaction, a saturated ammonium chloride aqueous solution and ethyl acetate were added to the reaction solution, so as to separate an organic layer. The organic layer was washed with a saturated sodium chloride aqueous solution and then dried over anhydrous magnesium sulfate. After removing the drying agent by filtration, the organic layer was concentrated under a reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate), so as to obtain 513 mg of the subject compound.

Workup

  1. customAfter completion of the reaction
  2. customso as to separate an organic layer
  3. washThe organic layer was washed with a saturated sodium chloride aqueous solution
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customAfter removing the drying agent
  6. filtrationby filtration
  7. concentrationthe organic layer was concentrated under a reduced pressure
  8. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-08b234732c854b23ad8c5f74401709b2
Source dataset
uspto-grants-2009_05
Patent number
US07538123B2

Reaction notes

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