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

HRID 429317

Reaction equation

HRID 429317 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

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).

Workup

  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

Sources & evidence

ORD record
ord-41084b0c456a40eaa0dae9ac6d0370c3
Source dataset
uspto-grants-2001_11
Patent number
US06316485B1

Linked notes

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