Réaction #6196

Équation de réaction

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

pivaloyl chloride

→

desired compound

Rendement 96.4%

4-[3-(pivaloylamino)propylthio]pyridine hydrochloride

Rendement 96.4%

Solvants

methylene chloride

Conditions de réaction

Traitement

1. 1
   Températurecooling
2. 2
   workup.STIRRINGthe mixture was 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 0.61 ml (4.96 mmol) of pivaloyl chloride under ice-cooling with stirring and the mixture was 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 1.01 g of the desired compound (free base) (96.4%, yellow oil).

Source