N-bromobutanimide → 6-Bromo-5-methoxy-2h-3,1-benzoxazine-2,4(1h)-dione

HRID 1725959Notes

Reaction equation

HRID 1725959 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[C:9](=[O:14])[O:10][C:11](=[O:13])[NH:12][C:7]=2[CH:6]=[CH:5][CH:4]=1.C1C(=O)N([Br:22])C(=O)C1>CN(C=O)C.ClCCl>[Br:22][C:4]1[CH:5]=[CH:6][C:7]2[NH:12][C:11](=[O:13])[O:10][C:9](=[O:14])[C:8]=2[C:3]=1[O:2][CH3:1]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 107502955-Methoxy-2H-3,1-benzoxazine-2,4(1H)-dione

Product 1

HCID 876056556-Bromo-5-methoxy-2h-3,1-benzoxazine-2,4(1h)-dioneYield 135.1%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

A solution of Example 385A (10.5 g, 54.4 mmol) in DMF (100 mL) and dichloromethane (200 mL) was cooled to 0° C., treated portionwise with NBS (14.4 g, 80.9 mmol) over 40 minutes, stirred overnight at room temperature and filtered. The filtrate was concentrated to provide the desired product (˜20 g) which was used directly in the next step.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-9e261719e8f943d080527d0fdf1c6d46
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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