Reacción #951206

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