Sodium hydride → Thiazolo[4,5-b]pyridine,2-[(2,2,2-trifluoroethyl)thio]-
Reaktionsgleichung
[H-].[Na+].[S:3]1[C:11]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[N:5]=[C:4]1[SH:12].C1(C)C=CC(S(O[CH2:23][C:24]([F:27])([F:26])[F:25])(=O)=O)=CC=1>CN(C)C=O>[F:25][C:24]([F:27])([F:26])[CH2:23][S:12][C:4]1[S:3][C:11]2[C:6]([N:5]=1)=[N:7][CH:8]=[CH:9][CH:10]=2Komponenten
Edukt 3
Produkt 1
Reagenzien, Katalysatoren, Lösungsmittel 1
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
A mixture of sodium hydride (60% suspension in oil, 0.72 g, 0.03 mol) in N,N-dimethylformamide is cooled to 0° C., treated dropwise with a solution of thiazolo[4,5-b]pyridine-2-thiol (5.0 g, 30 mmol) in N,N-dimethylformamide, stirred for 30 minutes, treated with a solution of 2,2,2-trifluoroethyl p-toluenesulfonate (3.81 g, 15 mmol) in N,N-dimethylformamide, heated to and stirred at 110° C. for 6 hours, and poured into an ice/water mixture. The resultant aqueous mixture is extracted with diethyl ether. The organic extract is washed with water, dried over anhydrous sodium sulfate, and concentrated in vacuo to obtain a residue. Column chromatography of the residue using an ethyl acetate/hexanes solution gives the title product as a light yellow liquid (2.91 g, 39% yield).
Aufarbeitung
- temperatureheated to and
- stirringstirred at 110° C. for 6 hours
- extractionThe resultant aqueous mixture is extracted with diethyl ether
- extractionThe organic extract
- washis washed with water
- dry with materialdried over anhydrous sodium sulfate
- concentrationconcentrated in vacuo
- customto obtain a residue
Quellen und Nachweise
- ORD-Eintrag
- ord-0a40d219543d41dbaf753419cdfcd12a
- Quelldatensatz
- uspto-grants-2002_09
- Patentnummer
- US06448262B1
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