Water → 6-Bromo-4-methyl-1,4-benzoxazin-3-one

HRID 1778698Notes

Reaction equation

HRID 1778698 reaction equation
[H-].[Na+].[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[NH:9][C:8]=2[CH:14]=1.[CH3:15]I.O>CN(C)C=O>[Br:3][C:4]1[CH:5]=[CH:6][C:7]2[O:12][CH2:11][C:10](=[O:13])[N:9]([CH3:15])[C:8]=2[CH:14]=1

Participants

6

Reactant 4

HCID 962WaterHCID 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

Sodium hydride (0.10 g, 2.6 mmol) was added to a solution of 6-bromo-2H-1,4-benzoxazin-3(4H)-one (0.49 g, 2.1 mmol) in N,N-dimethylformamide (3 mL) under nitrogen. After the mixture was stirred at r.t. for 10 min, methyl iodide (0.27 mL, 4.3 mmol) was added. The reaction mixture was stirred at r.t. for 1 h. Then 10 mL of water was added to the mixture, and a white precipitate was removed by filtration, washed with water, and dried under vacuum to afford the product which was directly used in next step reaction without further purification. LCMS (M+H)+=242.2/244.2.

Workup

  1. stirringThe reaction mixture was stirred at r.t. for 1 h
  2. customa white precipitate was removed by filtration
  3. washwashed with water
  4. customdried under vacuum
  5. customto afford the product which
  6. customwas directly used in next step reaction without further purification

Sources & evidence

ORD record
ord-4860fe20bc02423f80af4e193de3b613
Source dataset
uspto-grants-2016_02
Patent number
US09266892B2

Reaction notes

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