Réaction #1051268

Équation de réaction

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

benzoyl chloride

→

desired compound

Rendement 84.9%

4-[3-(benzoylamino)propylthio]pyridine

Rendement 84.9%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture stirred at room temperature for 30 minutes
3. 3
   LavageThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Autredried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   AutreThe residue was purified by column chromatography (eluent: ethyl acetate)

Mode opératoire

To a solution of 1.00 g (4.15 mmol) of 4-(3-aminopropylthio)pyridine dihydrochloride and 2.77 ml (19.8 mmol) of triethylamine in 40 ml of methylene chloride was added 0.58 ml (4.96 mmol) of benzoyl chloride under ice-cooling with stirring and the mixture stirred at room temperature for 30 minutes. The reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 960 mg of the desired compound (84.9%, colorless needles), mp: 120.0°-121.0° C.

Source