Potassium Carbonate → 5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde

HRID 47607

Reaction equation

Cl[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:13])[C:3]=1[CH:14]=[O:15].[Cl:16][C:17]1[CH:18]=[C:19]([SH:24])[CH:20]=[C:21]([Cl:23])[CH:22]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[Cl:16][C:17]1[CH:18]=[C:19]([S:24][C:2]2[N:6]([C:7]3[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=3)[N:5]=[C:4]([CH3:13])[C:3]=2[CH:14]=[O:15])[CH:20]=[C:21]([Cl:23])[CH:22]=1

Participants

Conditions

Temperature: 60 °C

Procedure

A solution containing 175 mg of 5-chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde, 142 mg of 3,5-dichlorothiophenol and 132 mg of potassium carbonate in 5 ml of anhydrous N,N-dimethylformamide was stirred under nitrogen at 60° C. for 2 h. The mixture was diluted with 10 ml of water and extracted three times with 8 ml of dichloromethane. The combined extracts were dried over magnesium sulphate, filtered and evaporated. The residue was purified by flash chromatography on silica gel using dichloromethane for the elution to give 164 mg of 5-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde as a yellow oil. Mass spectrum (EI) m/z 362 [M]+.

Workup

extractionextracted three times with 8 ml of dichloromethane
dry with materialThe combined extracts were dried over magnesium sulphate
filtrationfiltered
customevaporated
customThe residue was purified by flash chromatography on silica gel
washfor the elution

Sources & evidence

ORD record: ord-90718ffe606a452d909acb261ea027e3
Source dataset: uspto-grants-2004_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06699887B2

Linked notes

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