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

HRID 1078650Notes

Reaction equation

HRID 1078650 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 (50 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-3f499b3eee0540c6b01c89c58b8873f0
Source dataset
uspto-grants-1996_08
Patent number
US05550147

Reaction notes

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