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

HRID 47607

반응식

HRID 47607 반응식
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

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 6130275-Chloro-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehydeHCID 27360963,5-Dichlorobenzenethiol

생성물 1

HCID 227474725-(3,5-dichlorophenylthio)-3-methyl-1-phenyl-1H-pyrazole-4-carbaldehyde수율 56.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

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]+.

후처리

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

출처 및 근거

ORD 기록
ord-90718ffe606a452d909acb261ea027e3
출처 데이터셋
uspto-grants-2004_03
특허 번호
US06699887B2

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