Water → 2,2-Dimethyl-7-nitro-2H-benzo[b][1,4]oxazin-3(4H)-one

HRID 1479792Notes

Reaction equation

[NH2:1][C:2]1[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=1[OH:11].C(=O)([O-])[O-].[K+].[K+].Br[C:19]([CH3:26])([CH3:25])[C:20](OCC)=[O:21].O>CS(C)=O>[CH3:25][C:19]1([CH3:26])[C:20](=[O:21])[NH:1][C:2]2[CH:7]=[CH:6][C:5]([N+:8]([O-:10])=[O:9])=[CH:4][C:3]=2[O:11]1

Participants

Conditions

Temperature: 30 °C

Procedure

To a solution of 2-amino-5-nitrophenol (200 g) in dimethylsulfoxide (1000 mL) was added anhydrous potassium carbonate (269 g) under stirring at 30° C. or lower, then to the mixture was added ethyl 2-bromo-2-methylpropionate (278.4 g) at 30° C. or lower, and the mixture was stirred at 26° C. for 24 hours. To the reaction mixture was added water (2000 mL) at 40° C. or lower, and then stirred at room temperature for 3 hours. The reaction product was collected by filtration, and successively washed with dimethylsulfoxide/water (2:1, 800 mL) and water (3200 mL) to obtain the title compound (348.6 g) as a yellow solid (wet material) (yield: 121%, purity: 96%).

Workup

stirringlower, and the mixture was stirred at 26° C. for 24 hours
stirringlower, and then stirred at room temperature for 3 hours
filtrationThe reaction product was collected by filtration
washsuccessively washed with dimethylsulfoxide/water (2:1, 800 mL) and water (3200 mL)

Sources & evidence

ORD record: ord-245dd9fa679e4554bd9eb57887302e90
Source dataset: uspto-grants-2016_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09409874B2

Reaction notes

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