Methanol → 1-[2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]-1-ethanone

HRID 1166399Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1166399
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:10]=[C:11]([CH2:13][O:14]C3C=CC(C)=CC=3)[N:12]=2)=[CH:4][CH:3]=1.[CH3:32]O>[OH-].[Na+]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]([C:22]3[CH:27]=[CH:26][C:25]([S:28]([CH3:31])(=[O:30])=[O:29])=[CH:24][CH:23]=3)[CH:10]=[C:11]([C:13](=[O:14])[CH3:32])[N:12]=2)=[CH:6][CH:7]=1

Komponenten

4

Edukt 2

HCID 887MethanolHCID 229977132-(4-chlorophenyl)-4-[(4-methylphenoxy)methyl]-1-[4-(methylsulfonyl)phenyl]-1H-imidazole

Produkt 1

HCID 229977331-[2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl]-1-ethanone

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 14798Sodium HydroxideLösungsmittel

Versuchsvorschrift

A suspension of ethyl [2-(4-chlorophenyl)-1-[4-(methylsulfonyl)phenyl]-1H-imidazol-4-yl] carboxylate (Example 159) (929 mg, 2.29 mmol) in 16 ml of methanol and 16 ml of 1N aqueous sodium hydroxide was stirred at reflux for one hour. After cooling, the mixture was concentrated, water was added, and the resulting mixture was acidified with acetic acid. The mixture was extracted with dichloromethane, and the combined organic extracts were dried over sodium sulfate, filtered, and evaporated. Acetic acid was removed by azeotropic distillation with toluene to give the title compound, 520 mg, as a white crystalline solid: mp (DSC) 121° C. Anal. Calc'd. for C17H13ClN2O4S.H2O (MW 394.83): C, 51.71; H, 3.32; N, 7.10. Found: C, 51.89; H, 3.29; N, 6.97.

Aufarbeitung

  1. temperatureat reflux for one hour
  2. temperatureAfter cooling
  3. concentrationthe mixture was concentrated
  4. additionwater was added
  5. extractionThe mixture was extracted with dichloromethane
  6. dry with materialthe combined organic extracts were dried over sodium sulfate
  7. filtrationfiltered
  8. customevaporated
  9. customAcetic acid was removed by azeotropic distillation with toluene

Quellen und Nachweise

ORD-Eintrag
ord-a4c2285050f246bcbcc8cb7092468c68
Quelldatensatz
uspto-grants-2003_09
Patentnummer
US06613789B2

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