Potassium Carbonate → 1-[4-(4-Chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazole

HRID 463283

Reaktionsgleichung

Reaktionsgleichung von HRID 463283
Cl.[Cl:2][C:3]1[CH:8]=[CH:7][C:6]([CH2:9][CH2:10][CH:11](OS(C)(=O)=O)[CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:5][CH:4]=1.[C:23]([NH:26][C:27]1[CH:32]=[CH:31][C:30]([SH:33])=[CH:29][CH:28]=1)(=[O:25])[CH3:24].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O.CO>[Cl:2][C:3]1[CH:4]=[CH:5][C:6]([CH2:9][CH2:10][CH:11]([S:33][C:30]2[CH:29]=[CH:28][C:27]([NH:26][C:23](=[O:25])[CH3:24])=[CH:32][CH:31]=2)[CH2:12][N:13]2[CH:17]=[CH:16][N:15]=[CH:14]2)=[CH:7][CH:8]=1

Komponenten

6

Edukt 3

HCID 11430Potassium CarbonateHCID 707774'-MercaptoacetanilideHCID 202825741-[4-(4-Chlorophenyl)-2-(methanesulfonyloxy)-n-butyl]imidazole hydrochloride

Produkt 1

HCID 134573281-[4-(4-Chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazoleAusbeute 84 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 180AcetoneLösungsmittelHCID 887MethanolLösungsmittel

Versuchsvorschrift

A mixture of 1-[4-(4-chlorophenyl)-2-methanesulfonyloxy-n-butyl]imidazole hydrochloride (2.0 g), 4-acetylaminothiophenol (1.2 g) and anhydrous potassium carbonate (2.0 g) in 30 ml of acetone and 10 ml of methanol was stirred and refluxed overnight under nitrogen. The solvent was evaporated and the residue treated with water (50 ml) and ether (20 ml) and the mixture stirred until crystallization was complete. Filtration of the product and recrystallization from ethyl acetate gave 1.84 g of 1-[4-(4-chlorophenyl)-2-(4-acetylaminophenylthio)-n-butyl]imidazole as a pale cream solid, m.p. 165.5°-166.5° C. B. Similarly, proceeding as above substituting the appropriate thiophenol for 4-acetylaminothiophenol the following compounds are prepared:

Aufarbeitung

  1. temperaturerefluxed overnight under nitrogen
  2. customThe solvent was evaporated
  3. additionthe residue treated with water (50 ml) and ether (20 ml)
  4. stirringthe mixture stirred until crystallization
  5. filtrationFiltration of the product and recrystallization from ethyl acetate

Quellen und Nachweise

ORD-Eintrag
ord-4362c53482164d248c2e5f727147c609
Quelldatensatz
uspto-grants-1985_05
Patentnummer
US04518607

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