Reacción #216040

Ecuación de reacción

2,6-diethylaniline

3-(2-chlorophenyl)-5,6-dimethoxy-1-benzothiophen-2-carboxylic acid

diphenylphosphoryl azide

triethylamine

→

compound 102

Rendimiento 78.3%

N-[3-(2-Chlorophenyl)-5,6-dimethoxy-1-benzothiophen-2-yl]-N'-(2,6-diethylphenyl)urea

Rendimiento 78.3%

Disolventes

benzene

water

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturaheated
2. 2
   Temperaturaunder reflux for 30 minutes
3. 3
   TemperaturaAfter cooling
4. 4
   Temperaturaby refluxing for 2 hours
5. 5
   TemperaturaAfter cooling
6. 6
   Extracciónextracted with ethyl acetate
7. 7
   SecadoThe extract was dried over magnesium sulfate
8. 8
   workup.DISTILLATIONdistilled
9. 9
   Otroto remove the solvent
10. 10
    OtroThe crude product thus obtained
11. 11
    Otrowas purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7)

Procedimiento

To a stirred mixture of 500 mg of 3-(2-chlorophenyl)-5,6-dimethoxy-1-benzothiophen-2-carboxylic acid and 0.32 cc of diphenylphosphoryl azide in 5 cc of benzene was added dropwise 0.15 cc of triethylamine at room temperature. The resulting mixture was stirred at room temperature for 15 minutes and then heated under reflux for 30 minutes. After cooling, 0.245 cc of 2,6-diethylaniline was added, followed by refluxing for 2 hours. After cooling, water was added to the reaction mixture and extracted with ethyl acetate. The extract was dried over magnesium sulfate, and distilled to remove the solvent. The crude product thus obtained was purified by a silica gel column chromatography (eluent: ethyl acetate/hexane=3/7) to obtain 554 mg of compound 102.

Fuente