Sodium Hydroxide → 1-(4-Cyanophenyl)-5-[4-(methylsulfanyl)phenyl]-1H-pyrazole-3-carboxylic acid

HRID 1379106Notes

Reaction equation

HRID 1379106 reaction equation
[C:1]([C:3]1[CH:8]=[CH:7][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:22]([O:24]CC)=[O:23])=[N:10]2)=[CH:5][CH:4]=1)#[N:2].[OH-].[Na+]>C(O)C.O1CCCC1>[C:1]([C:3]1[CH:4]=[CH:5][C:6]([N:9]2[C:13]([C:14]3[CH:19]=[CH:18][C:17]([S:20][CH3:21])=[CH:16][CH:15]=3)=[CH:12][C:11]([C:22]([OH:24])=[O:23])=[N:10]2)=[CH:7][CH:8]=1)#[N:2]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 10761208HCID 10761208, compound

Product 1

HCID 229097231-(4-Cyanophenyl)-5-[4-(methylsulfanyl)phenyl]-1H-pyrazole-3-carboxylic acidYield 96.8%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

A mixture of ethyl 1-(4-cyanophenyl)-5-[4-(methylthio)phenyl]pyrazole-3-carboxylate (2.8 g) and 1N sodium hydroxide (10 ml) in ethanol (150 ml) and tetrahydrofuran (20 ml) was stirred at ambient temperature for 3 hours. The solvent was evaporated, and the residue was dissolved in water, acidified with hydrochloric acid, and extracted with ethyl acetate. The extract was washed with water, dried, and evaporated to give 1-(4-cyanophenyl)-5-[4-(methylthio)phenyl]pyrazole-3-carboxylic acid (2.5 g).

Workup

  1. customThe solvent was evaporated
  2. dissolutionthe residue was dissolved in water
  3. extractionextracted with ethyl acetate
  4. washThe extract was washed with water
  5. customdried
  6. customevaporated

Sources & evidence

ORD record
ord-0b8c9a47e71540acb07d11efe32fa00f
Source dataset
uspto-grants-1997_09
Patent number
US05670533

Reaction notes

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