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

HRID 1295997노트

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HRID 1295997 반응식
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]

참가 물질

5

반응물 3

HCID 78391,2-DibromoethaneHCID 11430Potassium CarbonateHCID 58910050N1-[5-Acetyl-3-(tert-butyl)-2-hydroxyphenyl]acetamide

생성물 1

HCID 589100091-[4-Acetyl-8-(tert-butyl)-3,4-dihydro-2H-1,4-benzoxazin-6-yl]-1-ethanone수율 98.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

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온도
70 °C

실험 절차

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.

후처리

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

출처 및 근거

ORD 기록
ord-60f155efce5e469c96346e7330c8e2e6
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07244730B2

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