Phenylhydrazine → 5-Amino-3-(methylsulfanyl)-1-phenyl-1H-pyrazole-4-carbonitrile

HRID 2392519Notes

Reaction equation

HRID 2392519 reaction equation
CS[C:3](=[C:6]([C:9]#[N:10])[C:7]#[N:8])[S:4][CH3:5].[C:11]1([NH:17][NH2:18])[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1>C(O)C>[NH2:8][C:7]1[N:17]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)[N:18]=[C:3]([S:4][CH3:5])[C:6]=1[C:9]#[N:10]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 992292-(Bis(methylsulfanyl)methylidene)propanedinitrile

Product 1

HCID 7367765-Amino-3-(methylsulfanyl)-1-phenyl-1H-pyrazole-4-carbonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprised of 17.0 g (100 mmol) of bis (methylthio)methylenepropanedinitrile, 10.8 g (100mmol) of phenylhydrazine and 80 ml of ethanol was heated under reflux for 2 hours. The solvent was removed through distillation, and 20 ml of ethanol was added to the residue, which was thus crystallized. The resulting crystals were taken out by means of filtration under suction to give 20.9 g (9.1 mmol) of the entitled product as colorless, needle-like crystals having a melting point of from 136° to 137° C. The yield was 91%.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for 2 hours
  3. customThe solvent was removed through distillation, and 20 ml of ethanol
  4. additionwas added to the residue, which
  5. customwas thus crystallized
  6. filtrationThe resulting crystals were taken out by means of filtration under suction

Sources & evidence

ORD record
ord-073e8d37d5aa4e2d8cc087ed9f099b74
Source dataset
uspto-grants-1998_09
Patent number
US05801008

Reaction notes

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