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

HRID 47613

Reaktionsgleichung

Reaktionsgleichung von HRID 47613
Cl[C:2]1[N:6]([CH2:7][C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)[N:5]=[C:4]([CH3:16])[C:3]=1[C:17]([C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1)=[O:18].C(=O)([O-])[O-].[K+].[K+].[Cl:31][C:32]1[CH:33]=[C:34]([SH:39])[CH:35]=[C:36]([Cl:38])[CH:37]=1>CN(C)C=O>[Cl:31][C:32]1[CH:33]=[C:34]([S:39][C:2]2[N:6]([CH2:7][C:8]3[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=3)[N:5]=[C:4]([CH3:16])[C:3]=2[C:17]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:18])[CH:35]=[C:36]([Cl:38])[CH:37]=1

Komponenten

5

Edukt 3

HCID 11430Potassium Carbonate3×HCID 27360963,5-Dichlorobenzenethiol3×HCID 22747458[5-chloro-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanone

Produkt 1

HCID 22747490[5-(3,5-dichlorophenylthio)-1-(4-methoxybenzyl)-3-methyl-1H-pyrazol-4-yl]-phenyl-methanoneAusbeute 58,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

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]+.

Aufarbeitung

  1. temperatureThe mixture was then heated at 50° C. for 64 h
  2. temperatureThe mixture was then heated at 100° C. for 2 h
  3. customThe solvent was removed under reduced pressure and residue
  4. custompartitioned between dichloromethane/water
  5. washwashed with brine
  6. dry with materialthen dried over anhydrous magnesium sulphate
  7. filtrationfiltered
  8. customevaporated
  9. customThe residue was purified via flash chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-c0e6a679e6c5490d93739aaac5a73549
Quelldatensatz
uspto-grants-2004_03
Patentnummer
US06699887B2

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