Methanol → Methyl 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoate

HRID 2293492Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 2293492
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([OH:25])=[O:24])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[Na].[OH-].[Na+].[CH3:31]O>Cl>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[N:9]=[C:10]([C:19]3[CH:27]=[CH:26][C:22]([C:23]([O:25][CH3:31])=[O:24])=[CH:21][CH:20]=3)[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)=[CH:6][CH:7]=1

Komponenten

6

Edukt 4

HCID 887MethanolHCID 14798Sodium HydroxideHCID 5360545SodiumHCID 110574684-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acid

Produkt 1

HCID 10133915Methyl 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]-benzoate

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 313Hydrochloric AcidKatalysator

Versuchsvorschrift

A mixture containing 4-[4-(4-fluorophenyl)-5-(4-pyridyl)-1H-imidazol-2-yl]benzoic acid, sodium salt (0.20 g, 0.5 mmol) [See Ex. 9 above] and concentrated HCl (10 drops) in MeOH (5 mL) was heated at reflux for 8 h. After cooling, the pH was adjusted to neutral by the addition of 2.5N NaOH, and the solid which formed was collected by filtration, washed with H2O and dried in vacuo. The title compound was obtained as a yellow solid (0.14 g, 76%) and was recrystallized from EtOAc/CH2Cl2 : 1H NMR (CDCl3 /MeOH-d4): δ8.36 (d, 2H); 8.03 (m, 4H); 7.60-7.30 (m, 4H); 7.07 (t, 2H); 3.84 (s,3H).

Aufarbeitung

  1. temperaturewas heated
  2. temperatureat reflux for 8 h
  3. temperatureAfter cooling
  4. customthe solid which formed
  5. filtrationwas collected by filtration
  6. washwashed with H2O
  7. customdried in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-e19110aa399f437686dab41aeb5e0b08
Quelldatensatz
uspto-grants-1997_11
Patentnummer
US05686455

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