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Water → 1-({4-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acid

HRID 1257363
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1257363
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([O:21]CC)=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[OH-].[Na+].O>C(O)C.O1CCCC1>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH2:13][N:14]3[CH:18]=[C:17]([C:19]([OH:21])=[O:20])[CH:16]=[N:15]3)[S:11][CH:12]=2)=[CH:4][C:3]=1[C:24]([F:27])([F:25])[F:26]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 962WaterHCID 14798Sodium HydroxideHCID 66939496ethyl 1-({4-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylate

Produkt 1

HCID 669395621-({4-[4-chloro-3-(trifluoromethyl)phenyl]-1,3-thiazol-2-yl}methyl)-1H-pyrazole-4-carboxylic acidAusbeute 26,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21873804
Tetrahydrofuran ethanol
Lösungsmittel

Versuchsvorschrift

To a mixed solution of the compound (270 mg, 0.66 mmol) obtained in Example 40a in ethanol/tetrahydrofuran (v/v=1/1, 8 ml) was added 2N aqueous sodium hydroxide solution (2.0 mL, 4.0 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the aqueous layer was washed with diethyl ether, neutralized with 1N aqueous hydrochloric acid solution, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure. The resulting crude title compound was recrystallized (ethanol-hexane) to give the title compound (67 mg, 18%) as pale-yellow crystals.

Aufarbeitung

  1. washthe aqueous layer was washed with diethyl ether
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained organic layer was washed with saturated brine
  4. dry with materialdried over anhydrous sodium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe resulting crude title compound was recrystallized (ethanol-hexane)

Quellen und Nachweise

ORD-Eintrag
ord-9c5dce0779c2411996f5ff6777c0f288
Quelldatensatz
uspto-grants-2013_06
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08461348B2

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