Reacción #6201

Ecuación de reacción

4-(3-aminopropylthio)pyridine dihydrochloride

triethylamine

4-anisoyl chloride

→

desired compound

Rendimiento 78.9%

4-[3-(4-methoxybenzoylamino)propylthio]pyridine

Rendimiento 78.9%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred for at room temperature for 30 minutes
3. 3
   LavadoThe reaction mixture was washed with an aqueous saturated sodium bicarbonate solution and water
4. 4
   Otrodried
5. 5
   workup.DISTILLATIONThe solvent was distilled off
6. 6
   OtroThe residue was purified by column chromatography (eluent: ethyl acetate)
7. 7
   Otroto obtain the powder which
8. 8
   Lavadowas washed with ether
9. 9
   Otrodried

Procedimiento

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 846 mg (4.96 mmol) of 4-anisoyl chloride under ice-cooling with stirring and the mixture was stirred for 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 the powder which was washed with ether and dried to obtain 990 mg of the desired compound (78.9%, colorless powder), mp: 121.0°-122.0° C.

Fuente