Triethylamine → 2-(4-Chlorobutylthio)pyridine

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).

1. temperaturecooling
2. stirringthe mixture was stirred at room temperature for 16 hours
3. distillationThe solvent was distilled off
4. dissolutionthe residue was dissolved in chloroform
5. washThe solution was washed with saturated aqueous sodium bicarbonate and water
6. customdried
7. distillationThe solvent was distilled off
8. customthe residue was purified by column chromatography (eluent:ethyl acetate/hexane=1:3)

ORD-Eintrag

ord-7ddc31d15fb34448b12245705a36cfb7

Quelldatensatz

uspto-grants-1996_10

DOI

10.6084/m9.figshare.5104873.v1

Patentnummer

US05561147