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

HRID 429317ノート

反応式

HRID 429317 の反応式
[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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
140 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-41084b0c456a40eaa0dae9ac6d0370c3
出典データセット
uspto-grants-2001_11
特許番号
US06316485B1

反応ノート

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