Reacción #6207

Ecuación de reacción

4-(3-aminopropylthio)pyridine

3,5-di-t-butyl-4-hydroxybenzoic acid

N-hydroxysuccinimide

1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride

→

desired compound

Rendimiento 27.3%

4-[3-(3,5-di-t-butyl-4-hydroxybenzoylamino)propylthio]pyridine

Rendimiento 27.3%

Disolventes

methylene chloride

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturacooling
2. 2
   workup.STIRRINGthe mixture was stirred at room temperature for 30 minutes
3. 3
   workup.STIRRINGthe mixture was stirred at rcom temperature for 8 hours
4. 4
   LavadoThe reaction mixture was washed with water
5. 5
   Otrodried
6. 6
   workup.DISTILLATIONThe solvent was distilled off
7. 7
   OtroThe residue was purified by column chromatography (eluent: ethyl acetate)

Procedimiento

To a solution of 1.49 g (5.94 mmol) of 3,5-di-t-butyl-4-hydroxybenzoic acid and 889 mg (7.73 mmol) of N-hydroxysuccinimide in 60 ml of methylene chloride was added 1.38 g (7.13 mmol) of 1-ethyl-3-(3-dimethylaminopropyl)carbodiimide hydrochloride under ice-cooling with stirring and the mixture was stirred at room temperature for 30 minutes. Further 1.00 g (5.94 mmol) of 4-(3-aminopropylthio)pyridine was added and the mixture was stirred at rcom temperature for 8 hours. The reaction mixture was washed with water and dried. The solvent was distilled off. The residue was purified by column chromatography (eluent: ethyl acetate) to obtain 650 mg of the desired compound (27.3%, colorless powder), mp: 203.0°-204.0° C.

Fuente