Ethanol → 4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid

HRID 925272Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 925272
C[O:2][C:3]([C:5]1[S:9][CH:8]=[N:7][C:6]=1[S:10][CH2:11][CH2:12][C:13]([F:22])([F:21])[C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)=[O:4].[OH-].[K+].CCO>CCO.O>[F:22][C:13]([F:21])([C:14]1[CH:19]=[CH:18][C:17]([F:20])=[CH:16][CH:15]=1)[CH2:12][CH2:11][S:10][C:6]1[N:7]=[CH:8][S:9][C:5]=1[C:3]([OH:4])=[O:2]

Komponenten

5

Edukt 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 867201694-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester

Produkt 1

HCID 867201704-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acidAusbeute 83 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 19096565Water ethanolLösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

4-[[3,3-Difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid methyl ester (0.88 g, 2.54 mmol) is taken in EtOH/water (1:1) (4 ml) powdered KOH (0.36 g, 6.34 mmol) is added. The mixture is refluxed vigorously at 120° C. for 16 h. After completion of the reaction, EtOH is evaporated. The residue is diluted with water (20 ml), acidified with 2M hydrochloric acid to pH 3, and extracted with EtOAc (3×30 ml). The combined organic layers are dried over sodium sulfate, evaporated to dryness yielding 4-[[3,3-difluoro-3-(4-fluorophenyl)-propyl]sulfanyl]-thiazole-5-carboxylic acid (0.7 g, 2.09 mmol, 83%).

Aufarbeitung

  1. additionis added
  2. customis evaporated
  3. additionThe residue is diluted with water (20 ml)
  4. extractionextracted with EtOAc (3×30 ml)
  5. dry with materialThe combined organic layers are dried over sodium sulfate
  6. customevaporated to dryness

Quellen und Nachweise

ORD-Eintrag
ord-1bc70a2ad4a64144987387616d326357
Quelldatensatz
uspto-grants-2016_03
Patentnummer
US09284286B2

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