Sodium Hydroxide → 2-(4-Fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)1-(thiazol-2-yl)ethoxy]benzoic acid

HRID 1251931Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1251931
[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH2:20][C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)=[CH:14][C:9]=2[C:10]([O:12]C)=[O:11])=[CH:4][CH:3]=1.[OH-].[Na+]>CO.O>[F:1][C:2]1[CH:33]=[CH:32][C:5]([CH2:6][CH2:7][C:8]2[CH:17]=[CH:16][C:15]([O:18][CH:19]([C:27]3[S:28][CH:29]=[CH:30][N:31]=3)[CH2:20][C:21]3[N:25]([CH3:26])[CH:24]=[N:23][CH:22]=3)=[CH:14][C:9]=2[C:10]([OH:12])=[O:11])=[CH:4][CH:3]=1

Komponenten

5

Edukt 2

HCID 14798Sodium HydroxideHCID 18324499Methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate

Produkt 1

HCID 183244782-(4-Fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)1-(thiazol-2-yl)ethoxy]benzoic acid

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

A mixture of methyl 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoate (2.07 g, 4.4 mmol) and sodium hydroxide (0.89 g, 22.23 mmol) in methanol (100 ml) and water (9 ml) was stirred under a nitrogen atmosphere at reflux for 18 hours, cooled to ambient temperature and the methanol evaporated off. The residue was treated with aqueous citric acid (1M, 40 ml) and extracted with dichloromethane. The organic extracts were dried and evaporated to dryness to give 2-(4-fluorophenethyl)-5-[2-(1-methylimidazol-5-yl)-1-(thiazol-2-yl)ethoxy]benzoic acid as a white foam, (1.48 g, 75%).

Aufarbeitung

  1. temperatureat reflux for 18 hours
  2. customthe methanol evaporated off
  3. additionThe residue was treated with aqueous citric acid (1M, 40 ml)
  4. extractionextracted with dichloromethane
  5. customThe organic extracts were dried
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-5609fe0ab1d2481e995b15e6743b1462
Quelldatensatz
uspto-grants-2002_01
Patentnummer
US06342765B1

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