Reaktion #5568

Reaktionsgleichung

5-mercaptoimidazo[1,2-a]pyridine

sodium methylate

3-methylsulfonylamino-1-methylsulfonyloxypropane

→

desired product

Ausbeute 47.5%

5-[3-(methylsulfonylamino)propylthio]imidazo[1,2-a]pyridine

Ausbeute 47.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturthe mixture was heated
2. 2
   Temperaturunder reflux for 16 hours
3. 3
   TemperaturAfter cooling
4. 4
   workup.DISTILLATIONthe solvent was distilled off
5. 5
   workup.DISSOLUTIONThe residue was dissolved in chloroform
6. 6
   Waschenwashed with an aqueous saturated sodium bicarbonate solution
7. 7
   Sonstigedried
8. 8
   workup.DISTILLATIONAfter the solvent was distilled off
9. 9
   Sonstigethe residue was purified by column chromatography [eluent: ethyl acetate/ethanol (50:1)]

Vorschrift

To a solution of 5-mercaptoimidazo[1,2-a]pyridine (1.50 g, 10 mmoles) and 4M sodium methylate (2.93 ml, 12 mmoles) in ethanol (50 ml) was added 3-methylsulfonylamino-1-methylsulfonyloxypropane (2.77 g, 12 mmoles) at room temperature and the mixture was heated under reflux for 16 hours. After cooling, the solvent was distilled off. The residue was dissolved in chloroform, washed with an aqueous saturated sodium bicarbonate solution and dried. After the solvent was distilled off, the residue was purified by column chromatography [eluent: ethyl acetate/ethanol (50:1)] to obtain 1.34 g of the desired product (47.5%, pale yellow crystals).

Quelle