Dimethylformamide → 1,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide

HRID 1874379

반응식

HRID 1874379 반응식
[OH:1][C:2]1[CH:3]=[C:4]([NH:8][C:9]([C:11]2[N:15]([CH3:16])[N:14]=[C:13]([CH3:17])[CH:12]=2)=[O:10])[CH:5]=[CH:6][CH:7]=1.Cl[C:19]1[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>O>[CH3:16][N:15]1[C:11]([C:9]([NH:8][C:4]2[CH:5]=[CH:6][CH:7]=[C:2]([O:1][C:19]3[CH:24]=[CH:23][C:22]([N+:25]([O-:27])=[O:26])=[CH:21][N:20]=3)[CH:3]=2)=[O:10])=[CH:12][C:13]([CH3:17])=[N:14]1

참가 물질

6

반응물 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 783082-Chloro-5-nitropyridineHCID 19481482N-(3-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide

생성물 1

HCID 577493821,3-dimethyl-N-{3-[(5-nitropyridin-2-yl)oxy]phenyl}-1H-pyrazole-5-carboxamide수율 98.3%

시약·촉매·용매 1

HCID 962Water용매

반응 조건

온도
60 °C

실험 절차

A mixture of N-(3-hydroxyphenyl)-1,3-dimethyl-1H-pyrazole-5-carboxamide (1.58 g, 6.83 mmol), 2-chloro-5-nitropyridine (1.03 g, 6.51 mmol), potassium carbonate (1.42 g, 10.2 mmol) and N,N-dimethylformamide (10 mL) was stirred at 60° C. for 15 hr. The reaction mixture was diluted with water and extracted with ethyl acetate. The organic layer was washed with water and saturated brine, dried over anhydrous magnesium sulfate and filtrated. The filtrate was concentrated under reduced pressure, and the residue was purified by column chromatography (hexane/ethyl acetate=70/30→0/100) to give the title compound (2.26 g, 94%) as a white solid.

후처리

  1. extractionextracted with ethyl acetate
  2. washThe organic layer was washed with water and saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. filtrationfiltrated
  5. concentrationThe filtrate was concentrated under reduced pressure
  6. customthe residue was purified by column chromatography (hexane/ethyl acetate=70/30→0/100)

출처 및 근거

ORD 기록
ord-418d69c0ffec416197ccf63349b6402e
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304557B2

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