Reaktion #438052

Reaktionsgleichung

potassium carbonate

3,5-dichlorothiophenol

potassium carbonate

3,5-dichlorothiophenol

potassium carbonate

3,5-dichlorothiophenol

[5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

→

[5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Ausbeute 58.1%

Lösungsmittel

N,N-dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe mixture was then heated at 50° C. for 64 h
2. 2
   TemperaturThe mixture was then heated at 100° C. for 2 h
3. 3
   SonstigeThe solvent was removed under reduced pressure and residue
4. 4
   Sonstigepartitioned between dichloromethane/water
5. 5
   Waschenwashed with brine
6. 6
   Trocknenthen dried over anhydrous magnesium sulphate
7. 7
   Filtrationfiltered
8. 8
   Sonstigeevaporated
9. 9
   SonstigeThe residue was purified via flash chromatography on silica gel

Vorschrift

A solution containing 170 mg of [5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone in 10 ml of N,N-dimethylformamide was treated with 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was heated at 100° C. for 4 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 50° C. for 64 h. The mixture was treated with a further 83 mg of potassium carbonate and 107 mg of 3,5-dichlorothiophenol. The mixture was then heated at 100° C. for 2 h. The solvent was removed under reduced pressure and residue partitioned between dichloromethane/water, washed with brine then dried over anhydrous magnesium sulphate, filtered and evaporated. The residue was purified via flash chromatography on silica gel using diethyl ether/petroleum ether (1:4 to 1:3) to give 140 mg of [5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone as a colourless oil. Mass spectrum (ES) m/z 483[M+H]+.

Quelle