Potassium Carbonate → 5-(3,5-dichlorophenylsulfanyl)-4-formyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester

HRID 1862463Notes

Reaction equation

HRID 1862463 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[O:12])=[C:9](Cl)[N:8]([CH:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5])[CH3:2].[Cl:17][C:18]1[CH:19]=[C:20]([SH:25])[CH:21]=[C:22]([Cl:24])[CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH2:1]([O:3][C:4]([C:6]1[C:10]([CH:11]=[O:12])=[C:9]([S:25][C:20]2[CH:21]=[C:22]([Cl:24])[CH:23]=[C:18]([Cl:17])[CH:19]=2)[N:8]([CH:14]([CH3:16])[CH3:15])[N:7]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27360963,5-DichlorobenzenethiolHCID 58907109Ethyl 5-chloro-4-formyl-1-isopropyl-1H-pyrazole-3-carboxylate

Product 1

HCID 867588885-(3,5-dichlorophenylsulfanyl)-4-formyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl esterYield 89.8%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution containing 6 g of 5-chloro-4-formyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester in 10 ml of anhydrous dimethyl formamide was treated at room temperature with 5.28 g of 3,5-dichlorothiophenol and 4.07 g of potassium carbonate. The mixture was then heated at 60° C. for 1 h before being left to cool to room temperature. The solvent removed under reduced pressure and the residue partitioned between dichloromethane and water. The organic extract was washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using diethyl ether/petoleum ether (1:4 to 1:3) for the elution to give 8.53 g of 5-(3,5-dichlorophenylthio)-4-formyl-1-isopropyl-1H-pyrazole-3-carboxylic acid ethyl ester as a yellow oil. Mass spectrum (ESI) m/z [M+H]+.

Workup

  1. waitbefore being left
  2. temperatureto cool to room temperature
  3. customThe solvent removed under reduced pressure
  4. customthe residue partitioned between dichloromethane and water
  5. extractionThe organic extract
  6. washwas washed with brine
  7. dry with materialthen dried over anhydrous magnesium sulphate
  8. filtrationfiltered
  9. customevaporated
  10. customThe residue was purified by flash chromatography on silica gel
  11. washfor the elution

Sources & evidence

ORD record
ord-40f3c4ea9d924931bf259e0040f23fd8
Source dataset
uspto-grants-2003_03
Patent number
US06538015B1

Reaction notes

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