Reaktion #978741

Reaktionsgleichung

1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine

potassium thioacetate

→

3-acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine

Ausbeute 75.0%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Sonstigeat room temperature
2. 2
   Sonstigethe completion of the reaction
3. 3
   Sonstigethe reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution
4. 4
   WaschenThe organic layer was washed with saturated aqueous sodium chloride solution
5. 5
   Trocknendried over anhydrous magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Einengenconcentrated under reduced pressure
8. 8
   SonstigeThe residue was purified by chromatography on a silica gel column

Vorschrift

To a solution of 1-(4-cyano-1,3-thiazol-2-yl)-3-methanesulfonyloxyazetidine (1.12 g, 4.32 mmol) (obtained as described in Reference Example 4(3)) in dimethylformamide (56 ml) was added potassium thioacetate (3.89 g, 27.0 mmol) at room temperature. The mixture was stirred in an oil bath (80° C.) for 4 hours. After checking the completion of the reaction, the reaction mixture was partitioned between ethyl acetate and saturated aqueous sodium hydrogencarbonate solution. The organic layer was washed with saturated aqueous sodium chloride solution, dried over anhydrous magnesium sulfate, filtered and concentrated under reduced pressure. The residue was purified by chromatography on a silica gel column using n-hexane:ethyl acetate (2:1) as the eluant to afford 3-acetylthio-1-(4-cyano-1,3-thiazol-2-yl)azetidine (0.767 g, yield 75%) as a pale brown solid.

Quelle