Potassium Carbonate → 5-(4-Fluorophenylthio)-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid

HRID 374421Notes

Reaction equation

HRID 374421 reaction equation
Cl[C:2]1[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=1[C:12]([OH:14])=[O:13].[F:15][C:16]1[CH:21]=[CH:20][C:19]([SH:22])=[CH:18][CH:17]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[F:15][C:16]1[CH:21]=[CH:20][C:19]([S:22][C:2]2[N:6]([CH3:7])[N:5]=[C:4]([C:8]([F:11])([F:10])[F:9])[C:3]=2[C:12]([OH:14])=[O:13])=[CH:18][CH:17]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 677894-FluorothiophenolHCID 27738065-Chloro-1-Methyl-3-(Trifluoromethyl)-1H-Pyrazole-4-Carboxylic Acid

Product 1

HCID 189969085-(4-Fluorophenylthio)-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acidYield 35%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 5-chloro-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid (2.0 g), 4-fluorothiophenol (1.66 g) and anhydrous potassium carbonate (3.26 g) was heated under reflux in acetonitrile with stirring for 4 hours. After filtration the filtrate was evaporated, acidified with dilute hydrochloric acid and extracted with ethyl acetate. The combined extract was dried (anydrous magnesium sulphate), filtered and evaporated in vacuo. Recrystallisation from ether/hexane gave 5-(4-fluorophenylthio)-1-methyl-3-trifluoromethylpyrazole-4-carboxylic acid (0.98 g) m.p. 190°-193.7° C. as a white solid.

Workup

  1. temperaturewas heated
  2. filtrationAfter filtration the filtrate
  3. customwas evaporated
  4. extractionextracted with ethyl acetate
  5. extractionThe combined extract
  6. dry with materialwas dried (anydrous magnesium sulphate)
  7. filtrationfiltered
  8. customevaporated in vacuo
  9. customRecrystallisation from ether/hexane

Sources & evidence

ORD record
ord-cf6e574266df4d439a20ca1f18876340
Source dataset
uspto-grants-1996_01
Patent number
US05480857

Reaction notes

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