Ammonium Hydroxide → 6-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one

HRID 1278687Notes

Reaction equation

HRID 1278687 reaction equation
[CH3:1][O:2][C:3]1[C:12]2[NH:11][C:10](=[O:13])[O:9][C:8]([CH3:15])([CH3:14])[C:7]=2[CH:6]=[CH:5][CH:4]=1.C([O-])(=O)C.[Na+].[Br:21]Br.[OH-].[NH4+]>C(O)(=O)C>[Br:21][C:5]1[CH:4]=[C:3]([O:2][CH3:1])[C:12]2[NH:11][C:10](=[O:13])[O:9][C:8]([CH3:15])([CH3:14])[C:7]=2[CH:6]=1

Participants

6

Reactant 4

HCID 14923Ammonium HydroxideHCID 24408BromineHCID 2106172H-3,1-Benzoxazin-2-one, 1,4-dihydro-4,4-dimethyl-8-methoxy-HCID 517045Sodium Acetate

Product 1

HCID 235096426-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-oneYield 93.4%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

To a mixture of 8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (2.1 g, 10.1 mmol), sodium acetate (1.5 g, 18 mmol) in acetic acid (30 mL) was added bromine (0.62 mL, 12 mmol) at ambient temperature. After 30 minutes, the solution was treated with a concentrated ammonium hydroxide solution (50 mL). The precipitate was collected on a filter and washed with water (3×20 mL) to yield 6-bromo-8-methoxy-4,4-dimethyl-1,4-dihydro-2H-3,1-benzoxazin-2-one (2.7 g, 93%) as off-white solid: MS (ESI) m/z 286, 288 [M +H]+.

Workup

  1. customThe precipitate was collected on
  2. filtrationa filter
  3. washwashed with water (3×20 mL)

Sources & evidence

ORD record
ord-4778dc075ee64ab093fa833b1594dd50
Source dataset
uspto-grants-2002_09
Patent number
US06444668B1

Reaction notes

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