Reacción #361908

Ecuación de reacción

water

4-(4-chlorobutylthio)pyridine

sodium hydride

3-[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin

→

desired product

Rendimiento 80.7%

1,3-bis[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin

Rendimiento 80.7%

Disolventes

dimethylformamide

Condiciones de reacción

Tratamiento posterior

1. 1
   workup.ADDITIONwas added
2. 2
   workup.STIRRINGwith stirring under ice-
3. 3
   Temperaturacooling
4. 4
   workup.STIRRINGthe mixture was stirred at 80° C. for 16 hours
5. 5
   TemperaturaAfter cooling
6. 6
   Extracciónthe mixture was extracted with ethyl acetate
7. 7
   OtroThe extract was dried
8. 8
   workup.DISTILLATIONthe-solvent was distilled off
9. 9
   OtroThe residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1)

Procedimiento

To a suspension of 96 mg (2.4 mmol) of 60% sodium hydride (oily) in 15 ml of dimethylformamide, 587 mg (2.0 mmol) of 3-[4-(4-pyridylthio)butyl]-5,5-dimethylhydantoin was added, and the mixture was stirred at room temperature for 10 minutes. To this reaction mixture, 807 mg (4.0 mmol) of 4-(4-chlorobutylthio)pyridine was added with stirring under ice-cooling, and the mixture was stirred at 80° C. for 16 hours. After cooling, water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The extract was dried and the-solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate/ethanol=10:1) to give 0.74 g of the desired product (80.7% yield, yellow oil).

Fuente