Water → 6-Bromo-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dione

HRID 908549Notes

Reaction equation

HRID 908549 reaction equation
[Br:1][C:2]1[CH:13]=[C:6]2[C:7]([O:9][C:10](=[O:12])[NH:11][C:5]2=[CH:4][CH:3]=1)=[O:8].[H-].[Na+].I[CH3:17].O>CN(C=O)C.ClCCl>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[N:11]([CH3:17])[C:10](=[O:12])[O:9][C:7](=[O:8])[C:6]=2[CH:13]=1

Participants

7

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2885615-Bromoisatoic Anhydride

Product 1

HCID 176065836-Bromo-1-methyl-2H-3,1-benzoxazine-2,4(1H)-dioneYield 51.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

5-bromoisatoic anhydride (3 g, 12 mmol) was stirred in 50 mL of DMF at 0° C. and sodium hydride (60% dispersion in mineral oil) (0.4 g, 15 mmol) was added in portions, with stirring for 1 hour at room temperature. Iodomethane (0.8 mL, 12 mmol) was added drop wise and the reaction mixture was allowed to stir for 4 hours. Water (50 mL) was added slowly and 50 mL of Dichloromethane (DCM) was also added. A white solid precipitated out and was filtered off. The layers were separated layers. Aqueous layer extracted with DCM (2×25 ml). The combined organic layers were extracted with water (4×25 ml) and once with brine (25 ml). The organic layer was dried with MgSO4 and the solvent removed. The residue was purified by flash chromatography (0-3% MeOH/DCM) to afford 1.57 g of product. Yield 49%

Workup

  1. stirringto stir for 4 hours
  2. customA white solid precipitated out and
  3. filtrationwas filtered off
  4. customThe layers were separated layers
  5. extractionAqueous layer extracted with DCM (2×25 ml)
  6. extractionThe combined organic layers were extracted with water (4×25 ml) and once with brine (25 ml)
  7. dry with materialThe organic layer was dried with MgSO4
  8. customthe solvent removed
  9. customThe residue was purified by flash chromatography (0-3% MeOH/DCM)

Sources & evidence

ORD record
ord-f676b15974d04e83a9cc5e063e4e4b2a
Source dataset
uspto-grants-2011_09
Patent number
US08017626B2

Reaction notes

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