Methyl iodide → 6-Bromo-4-methyl-1,4-benzoxazin-3-one

HRID 216928

Reaction equation

HRID 216928 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[NH:11][C:6]=2[CH:5]=1.[CH3:15]I>CN(C=O)C>[Br:3][C:4]1[CH:14]=[CH:13][C:7]2[O:8][CH2:9][C:10](=[O:12])[N:11]([CH3:15])[C:6]=2[CH:5]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 162181426-Bromo-2H-1,4-benzoxazin-3(4H)-one

Product 1

HCID 532173836-Bromo-4-methyl-1,4-benzoxazin-3-one

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To sodium hydride (63 mg) in DMF (3 mL) under an atmosphere of nitrogen was added 6-bromo-2H-benzo[b][1,4]oxazin-3(4H)-one (0.3 g) and the mixture was stirred at room temperature for 1 h. Methyl iodide (0.123 mL) was added and the mixture was stirred overnight at room temperature. The mixture was poured onto ice/water and extracted into ethyl acetate (×2). The ethyl acetate was washed with water (×3), dried and the solvent was evaporated. The resulting material was purified by chromatography on silica eluting with 10% ethyl acetate/isohexane to afford the sub-titled compound (299 mg).

Workup

  1. stirringthe mixture was stirred overnight at room temperature
  2. additionThe mixture was poured onto ice/water
  3. extractionextracted into ethyl acetate (×2)
  4. washThe ethyl acetate was washed with water (×3)
  5. customdried
  6. customthe solvent was evaporated
  7. customThe resulting material was purified by chromatography on silica eluting with 10% ethyl acetate/isohexane

Sources & evidence

ORD record
ord-15e1c4e7f27d4b5d82625a4267c0c832
Source dataset
uspto-grants-2012_06
Patent number
US08193239B2

Linked notes

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