Phenylhydrazine → Ethyl 5-amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carboxylate

HRID 1024597Notes

Reaction equation

HRID 1024597 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]([C:11]#[N:12])=[C:6](SC)[S:7][CH3:8])[CH3:2].[C:14]1([NH:20][NH2:21])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>C(O)C>[CH2:1]([O:3][C:4]([C:5]1[C:6]([S:7][CH3:8])=[N:21][N:20]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:11]=1[NH2:12])=[O:13])[CH3:2]

Participants

4

Reactant 2

HCID 7516PhenylhydrazineHCID 2747745Ethyl 3,3-Bis(methylthio)-2-cyanoacrylate

Product 1

HCID 5189818Ethyl 5-amino-3-(methylthio)-1-phenyl-1H-pyrazole-4-carboxylate

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 2-cyano-3,3-bis-methylsulfanyl-acrylic acid ethyl ester (5.00 g, 23.0 mmol) in dry ethanol (100 mL) is added phenylhydrazine (2.28 mL, 23.0 mmol). The reaction mixture is heated to reflux for 2 h before removal of the solvent. The resulting solid is recrystallized from EtOH (20 mL) to provide 5-amino-3-methylsulfanyl-1-phenyl-1H-pyrazole-4-carboxylic acid ethyl ester as a white solid product; HPLC-MS calculated for C13H15N3O2S (M+H+) 278.1, found 278.1.

Workup

  1. temperatureThe reaction mixture is heated
  2. temperatureto reflux for 2 h before removal of the solvent
  3. customThe resulting solid is recrystallized from EtOH (20 mL)

Sources & evidence

ORD record
ord-987238e166db4a6380296d2a9584980f
Source dataset
uspto-grants-2014_05
Patent number
US08722691B2

Reaction notes

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