Sodium hydride → methyl 3,4-dihydro-2-isopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

HRID 622364Notes

Reaction equation

HRID 622364 reaction equation
[CH:1]([CH:4]1[C:9](=[O:10])[NH:8][C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5]1)([CH3:3])[CH3:2].[H-].[Na+].Br[CH2:18][C:19]([O:21][CH3:22])=[O:20]>CN(C)C=O.O>[CH:1]([CH:4]1[C:9](=[O:10])[N:8]([CH2:18][C:19]([O:21][CH3:22])=[O:20])[C:7]2[CH:11]=[CH:12][CH:13]=[CH:14][C:6]=2[O:5]1)([CH3:3])[CH3:2]

Participants

6

Reactant 3

HCID 24758Sodium hydrideHCID 60984Methyl bromoacetateHCID 128935222-isopropyl-4H-benzo[1,4]oxazin-3-one

Product 1

HCID 14234696methyl 3,4-dihydro-2-isopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of 2-isopropyl-2H-1,4-benzoxazin-3(4H)-one (19.1 g) in N,N-dimethylformamide (200 ml), sodium hydride (60% in oil, 4.0 g) was added and stirred at room temperature for 30 minutes, to which a solution of methyl bromoacetate (10 ml) in N,N-dimethylformamide (200 ml) was added dropwise with ice-cooling. After stirring with ice-cooling for 1 hour, the reaction mixture was diluted with water and subjected to extraction with ethyl acetate. The extract was washed with water, dried (MgSO4) and evaporated to dryness, to give methyl 3,4-dihydro-2-isopropyl-3-oxo-2H-1,4-benzoxazine-4-acetate as an oil. Yield was 26.0 g (98.9%).

Workup

  1. additionwas added dropwise with ice-
  2. temperaturecooling
  3. temperaturecooling for 1 hour
  4. extractionsubjected to extraction with ethyl acetate
  5. washThe extract was washed with water
  6. dry with materialdried (MgSO4)
  7. customevaporated to dryness

Sources & evidence

ORD record
ord-0fa8d426acb348ff8741074401c7d234
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

Loading…