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Ethanedioyl dibromide → 3-bromo-6-methyl-1-(3-(trifluoromethyl)phenyl)pyrazin-2(1H)-one

HRID 1259327
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HRID 1259327 반응식
[CH3:1][C:2]1[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:6](=[O:18])[C:5](=O)[NH:4][CH:3]=1.C(Br)(=O)C([Br:23])=O>CN(C=O)C.ClCCCl>[Br:23][C:5]1[C:6](=[O:18])[N:7]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([C:14]([F:17])([F:16])[F:15])[CH:9]=2)[C:2]([CH3:1])=[CH:3][N:4]=1
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참가 물질

5

반응물 2

HCID 84841Ethanedioyl dibromide2회HCID 59564946HCID 59564946, 화합물

생성물 1

HCID 584327923-bromo-6-methyl-1-(3-(trifluoromethyl)phenyl)pyrazin-2(1H)-one수율 93%

시약·촉매·용매 2

HCID 6228Dimethylformamide촉매2회HCID 111,2-Dichloroethane용매

실험 절차

6-Methyl-1-[3-(trifluoromethyl)phenyl]-1,4-dihydropyrazine-2,3-dione (0.52 g, 1.92 mmol) and 1,2-dichloroethane (10 ml) were placed in a vial (20 ml). To the resulting suspension was added carefully oxalyl bromide (0.53 ml, 1.24 g, 5.75 mmol). A foam was formed during the addition, and as the foam was settling down the stirring was started. DMF (3 drops) was added and the vial was sealed and the mixture was stirred overnight. Another portion of oxalyl bromide (0.2 ml, 0.46 g, 2.23 mmol) and DMF (3 drops) was added and the reaction was run for another 24 h. The mixture was partitioned between is DCM (20 ml) and water (20 ml) and the organic phase was dried. Filtration and evaporation gave a crude product, which was purified on silica, affording 3-bromo-6-methyl-1-[3-(trifluoromethyl)phenyl]pyrazin-2(1H)-one (0.59 g, 93%).

후처리

  1. customA foam was formed during the addition
  2. customthe vial was sealed
  3. waitthe reaction was run for another 24 h
  4. customThe mixture was partitioned
  5. customthe organic phase was dried
  6. filtrationFiltration and evaporation
  7. customgave a crude product, which
  8. customwas purified on silica

출처 및 근거

ORD 기록
ord-35556f5ffe224bfe8b8bf38448c3649c
출처 데이터셋
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08466284B2

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