1,2-Dibromoethane → 1-[4-Acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone

HRID 1295997Notes

Reaction equation

C(=O)([O-])[O-].[K+].[K+].Br[CH2:8][CH2:9]Br.[C:11]([C:14]1[CH:15]=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]([OH:24])=[C:18]([NH:20][C:21](=[O:23])[CH3:22])[CH:19]=1)(=[O:13])[CH3:12]>CN(C)C=O>[C:21]([N:20]1[C:18]2[CH:19]=[C:14]([C:11](=[O:13])[CH3:12])[CH:15]=[C:16]([C:25]([CH3:28])([CH3:27])[CH3:26])[C:17]=2[O:24][CH2:9][CH2:8]1)(=[O:23])[CH3:22]

Participants

Conditions

Temperature: 70 °C

Procedure

Potassium carbonate (113 g, 818 mmol) and 1,2-dibromoethane (64.1 g, 341 mmol) were added to a solution of the N1-[5-acetyl-3-(tert-butyl)-2-hydroxyphenyl]acetamide (34.0 g, 137 mmol) in dimethylformamide (280 ml) under a nitrogen atmosphere, and then the mixture was stirred at 70° C. for 17 hours. The solvent was distilled off under reduced pressure, ethyl acetate was added to the residue and the mixture was washed with water (3 times) and brine in that order. After drying over anhydrous magnesium sulfate, the solvent was distilled off under reduced pressure to yield the title compound (36.9 g, 98.1% yield) as light red crystals. These were used without purification for the following reaction.

Workup

distillationThe solvent was distilled off under reduced pressure, ethyl acetate
additionwas added to the residue
washthe mixture was washed with water (3 times) and brine in that order
dry with materialAfter drying over anhydrous magnesium sulfate
distillationthe solvent was distilled off under reduced pressure

Sources & evidence

ORD record: ord-60f155efce5e469c96346e7330c8e2e6
Source dataset: uspto-grants-2007_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07244730B2

Reaction notes

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