Reaktion #6261

Reaktionsgleichung

4-(4-aminobutylthio)pyridine

triethylamine

benzoyl chloride

→

desired compound

Ausbeute 34.4%

4-[4-(benzoylamino)butylthio]pyridine

Ausbeute 34.4%

Lösungsmittel

methylene chloride

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturcooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 13 hours
3. 3
   WaschenThe mixture was washed with saturated aqueous sodium bicarbonate and saturated saline
4. 4
   Trocknendried over anhydrous magnesium sulfate
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   Sonstigethe residue was purified by column chromatography (eluent: ethyl acetate)

Vorschrift

To a solution of 1.00 g (5.49 mmol) of 4-(4-aminobutylthio)pyridine and 0.92 ml (6.60 mmol) of triethylamine in 30 ml of methylene chloride, 0.67 ml (5.77 mmol) of benzoyl chloride was added with stirring under ice-cooling and the mixture was stirred at room temperature for 13 hours. The mixture was washed with saturated aqueous sodium bicarbonate and saturated saline, and dried over anhydrous magnesium sulfate. The solvent was distilled off and the residue was purified by column chromatography (eluent: ethyl acetate) to give 0.54 g of the desired compound (34.4% yield, colorless crystals), mp. 75°-77° C.

Quelle