Reaktion #6268

Reaktionsgleichung

2-mercaptopyridine

triethylamine

1-bromo-4-chlorobutane

→

desired compound

Ausbeute 65.5%

2-(4-chlorobutylthio)pyridine

Ausbeute 65.5%

Lösungsmittel

ethanol

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 16 hours
3. 3
   workup.DISTILLATIONThe solvent was distilled off
4. 4
   workup.DISSOLUTIONthe residue was dissolved in chloroform
5. 5
   WaschenThe solution was washed with saturated aqueous sodium bicarbonate and water
6. 6
   Sonstigedried
7. 7
   workup.DISTILLATIONThe solvent was distilled off
8. 8
   Sonstigethe residue was purified by column chromatography (eluent: ethyl acetate/hexane =1:3)

Vorschrift

To a solution of 25.0 g (225 mmol) of 2-mercaptopyridine and 34.5 ml (247 mmol) of triethylamine in 300 ml of ethanol, 28.5 ml (247 mmol) of 1-bromo-4-chlorobutane was added with stirring under ice-cooling, and the mixture was stirred at room temperature for 16 hours. The solvent was distilled off and the residue was dissolved in chloroform. The solution was washed with saturated aqueous sodium bicarbonate and water, and dried. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate/hexane =1:3) to give 29.73 g of the desired compound (65.5% yield, pale yellow oil).

Quelle