Dimethylformamide → 2-isopropyl-4H-benzo[1,4]oxazin-3-one

HRID 622373Notes

Reaction equation

HRID 622373 reaction equation
Br[CH:2]([CH:13]([CH3:15])[CH3:14])[C:3]([NH:5][C:6]1[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=1[OH:12])=[O:4].C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH:13]([CH:2]1[C:3](=[O:4])[NH:5][C:6]2[CH:11]=[CH:10][CH:9]=[CH:8][C:7]=2[O:12]1)([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 142346662-(2-Bromo-3-methylbutyryl)aminophenol

Product 1

HCID 128935222-isopropyl-4H-benzo[1,4]oxazin-3-one

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 2-(2-bromo-3-methylbutyryl)aminophenol (58.0 g), powdered potassium carbonate (38.3 g) and N,N-dimethylformamide (200 ml) was stirred at room temperature for 2 hours. The mixture was diluted with water and the precipitate was collected to yield 2-isopropyl-2H-1,4-benzoxazin-3(4H)-one as crystals. Yield was 38.1 g (93.4%). Recrystallization from ethanol gave colorless plates, mp 118°-119° C. In the same manner as in Reference Example 1, the following compounds were obtained.

Workup

  1. customthe precipitate was collected

Sources & evidence

ORD record
ord-c005a984bff04c519c9d09cbf1d0813b
Source dataset
uspto-grants-1988_09
Patent number
US04771050

Reaction notes

Loading…