Reaktionsgleichung
[CH3:1][O:2][CH2:3][C:4](Cl)=O.[NH2:7][C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[SH:18])=[CH:15][CH:14]=[CH:13][CH:12]=2.[OH-].[Na+]>COCC(O)=O.O.ClCCl>[CH3:1][O:2][CH2:3][C:4]1[S:18][C:17]2[C:16]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[N:10]=[CH:9][C:8]=2[N:7]=1Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 3
Reaktionsbedingungen
- Temperatur
- 140 °C
Versuchsvorschrift
Methoxyacetyl chloride (1.8 mL) was added to a mixture of 3-aminoquinoline-4-thiol (2.8 g) in methoxyacetic acid (15 mL). The reaction was heated at about 140° C. for 1 hour and then allowed to cool to ambient temperature. The reaction mixture was diluted with a small amount of water, made basic with 10% sodium hydroxide and then extracted with dichloromethane (300 mL). The extract was washed with sodium bicarbonate, washed with water, dried over magnesium sulfate and then concentrated under vacuum to provide crude product as a dark oil. The oil was dissolved in dichloromethane and then placed on a layer of silica gel. The silica gel was eluted with 1:1 hexane:ethyl acetate. The eluant was concentrated under vacuum to provide 2.3 g of 2-(methoxymethyl)thiazolo[4,5-c]quinoline as an orange solid.
Aufarbeitung
- temperatureto cool to ambient temperature
- extractionextracted with dichloromethane (300 mL)
- washThe extract was washed with sodium bicarbonate
- washwashed with water
- dry with materialdried over magnesium sulfate
- concentrationconcentrated under vacuum
- customto provide crude product as a dark oil
- washThe silica gel was eluted with 1:1 hexane
- concentrationThe eluant was concentrated under vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-0795e61358bb43e2880c43b4130bad78
- Quelldatensatz
- uspto-grants-2004_03
- Patentnummer
- US06703402B2
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