(3-Methoxyphenyl)hydrazine → {1-(3-Methoxyphenyl)-5-[4-(methylthio)-phenyl]pyrazol-3-yl}amine

HRID 429317

반응식

HRID 429317 반응식
[CH3:1][O:2][C:3]1[CH:4]=[C:5]([NH:9][NH2:10])[CH:6]=[CH:7][CH:8]=1.[CH3:11][S:12][C:13]1[CH:18]=[CH:17][C:16]([CH:19]=[CH:20][C:21]#[N:22])=[CH:15][CH:14]=1.C[O-].[Na+]>CO>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([N:9]2[C:19]([C:16]3[CH:17]=[CH:18][C:13]([S:12][CH3:11])=[CH:14][CH:15]=3)=[CH:20][C:21]([NH2:22])=[N:10]2)[CH:6]=[CH:7][CH:8]=1

참가 물질

5

반응물 3

HCID 423605(3-Methoxyphenyl)hydrazineHCID 42396803-[4-(Methylthio)phenyl]acrylonitrileHCID 10942334Sodium Methoxide

생성물 1

HCID 18355402{1-(3-Methoxyphenyl)-5-[4-(methylthio)-phenyl]pyrazol-3-yl}amine수율 51.3%

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
140 °C

실험 절차

To a mixture of (3-methoxyphenyl)hydrazine (6 g) and 3-[4-(methylthio)phenyl]acrylonitrile (5.7 g) in methanol (100 ml) was added sodium methoxide (28 wt. % solution in methanol) (18 ml) at ambient temperature. The mixture was heated to dryness under nitrogen at 140° C. for 30 minutes. The resultant orange mass was partitioned between dichloromethane and ice water. The organic layer was dried over magnesium sulfate, and then filtered. This filtrate was evaporated in vacuo. The resultant mass was dissolved in ethyl acetate (150 ml) and refluxed for 1 hour in the presence of magnesium (IV) oxide (20 g). This mixture was cooled, and filtered. The filtrate was evaporated in vacuo. The resultant mass was purified by column chromatography on silica gel using dichloromethane as eluent to give {1-(3-methoxyphenyl)-5-[4-(methylthio)-phenyl]pyrazol-3-yl}amine (5.2 g).

후처리

  1. customThe resultant orange mass was partitioned between dichloromethane and ice water
  2. dry with materialThe organic layer was dried over magnesium sulfate
  3. filtrationfiltered
  4. customThis filtrate was evaporated in vacuo
  5. dissolutionThe resultant mass was dissolved in ethyl acetate (150 ml)
  6. temperaturerefluxed for 1 hour in the presence of magnesium (IV) oxide (20 g)
  7. temperatureThis mixture was cooled
  8. filtrationfiltered
  9. customThe filtrate was evaporated in vacuo
  10. customThe resultant mass was purified by column chromatography on silica gel

출처 및 근거

ORD 기록
ord-41084b0c456a40eaa0dae9ac6d0370c3
출처 데이터셋
uspto-grants-2001_11
특허 번호
US06316485B1

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