Potassium Carbonate → 2-(2-(Phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid
Reaktionsgleichung
C([O-])([O-])=O.[K+].[K+].[C:7]1([S:13]([CH2:16][CH2:17][SH:18])(=[O:15])=[O:14])[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=1.Cl[C:20]1[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]2[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:36])([F:35])[F:34])[CH:26]=2)[N:21]=1>CC(C)=O>[C:7]1([S:13]([CH2:16][CH2:17][S:18][C:20]2[C:29]([C:30]([OH:32])=[O:31])=[CH:28][C:27]3[C:22](=[CH:23][CH:24]=[C:25]([C:33]([F:34])([F:36])[F:35])[CH:26]=3)[N:21]=2)(=[O:15])=[O:14])[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=1Komponenten
5
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 70 °C
Versuchsvorschrift
206 mg (1.5 mmol) K2CO3 and 303 mg (1.5 mmol) 2-(phenylsulfonyl)ethanethiol were added to a solution of 827 mg (1.0 mmol) 2-chloro-6-(trifluoromethyl)quinoline-3-carboxylic acid (precursor VVV03) in acetone (3 ml) and the mixture was heated for 5 h at 70° C. Then it was filtered and the filtrate was concentrated to small volume under vacuum. The residue was dissolved in water and acidified with a 1N hydrochloric acid. It was then extracted with EE and the organic phase was dried over Na2SO4, filtered and concentrated to small volume under vacuum. Crystallisation (DCM/hexane) of the residue yielded 316 mg (0.7 mmol, 72%) 2-(2-(phenylsulfonyl)ethylthio)-6-(trifluoromethyl)quinoline-3-carboxylic acid.
Aufarbeitung
- filtrationThen it was filtered
- concentrationthe filtrate was concentrated to small volume under vacuum
- dissolutionThe residue was dissolved in water
- extractionIt was then extracted with EE
- dry with materialthe organic phase was dried over Na2SO4
- filtrationfiltered
- concentrationconcentrated to small volume under vacuum
- customCrystallisation (DCM/hexane) of the residue
Quellen und Nachweise
- ORD-Eintrag
- ord-88758ace43f74dcdb759344c5a002fd1
- Quelldatensatz
- uspto-grants-2013_03
- Patentnummer
- US08399673B2
Notizen zur Reaktion
Wird geladen…