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Dimethylformamide → 1-(3-Bromophenyl)-5-methyl-1h-pyrazole-3-carboxamide

HRID 733123
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HRID 733123 반응식
[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[CH:12]=[CH:11][C:10](C(O)=O)=[N:9]2)[CH:5]=[CH:6][CH:7]=1.[C:16]([O-])(=O)C.[NH4+].C[N:22]([CH:24]=[O:25])C>>[Br:1][C:2]1[CH:3]=[C:4]([N:8]2[C:12]([CH3:16])=[CH:11][C:10]([C:24]([NH2:22])=[O:25])=[N:9]2)[CH:5]=[CH:6][CH:7]=1
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참가 물질

4

반응물 3

HCID 6228DimethylformamideHCID 517165Ammonium AcetateHCID 431246391-(3-Bromophenyl)-1H-pyrazole-3-carboxylic acid

생성물 1

HCID 574282521-(3-Bromophenyl)-5-methyl-1h-pyrazole-3-carboxamide수율 82%

실험 절차

To a solution of the carboxylic acid (3.79 g, 14.1 mmol) in DMF (47 ml) was added 1,1-carbonyldiimidazole (3.45 g, 21.2 mmol) and the mixture was stirred at room temperature for 3 hours. Anhydrous ammonium acetate (10.9 g, 141 mmol) was then added and the reaction was stirred at room temperature for an additional 16 hours. The reaction mixture was partitioned between ethylacetate and saturated sodium bicarbonate. The organic phase was washed with water, brine, then dried over sodium sulfate and concentrated. The crude product obtained was purified by silica-gel column chromatography (2:3 hexanes/ethyl acetate) to give the product as a white solid (3.23 g, 82%).

후처리

  1. stirringthe reaction was stirred at room temperature for an additional 16 hours
  2. customThe reaction mixture was partitioned between ethylacetate and saturated sodium bicarbonate
  3. washThe organic phase was washed with water, brine
  4. dry with materialdried over sodium sulfate
  5. concentrationconcentrated
  6. customThe crude product obtained
  7. customwas purified by silica-gel column chromatography (2:3 hexanes/ethyl acetate)

출처 및 근거

ORD 기록
ord-5998c582096346eab508f7f01d9c7082
출처 데이터셋
uspto-grants-2009_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07589116B2

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