Reacción #1005954

Ecuación de reacción

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazole-5-carboxylic acid

Thionyl chloride

→

title compound

Rendimiento 65.0%

{2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)-pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazol-5-yl}methanol

Rendimiento 65.0%

Disolventes

1,2-dichloroethane

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawas then refluxed
2. 2
   Temperaturaunder heating for 5 hours
3. 3
   OtroAfter removing the solvent
4. 4
   Otroby evaporation
5. 5
   workup.DISSOLUTIONthe residues were dissolved in 1,4-dioxane (20 mL)
6. 6
   workup.ADDITIONadded dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling
7. 7
   workup.ADDITIONAfter the dropwise addition
8. 8
   Temperaturathe reaction solution was refluxed
9. 9
   Temperaturaunder heating for one hour
10. 10
    TemperaturaAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    Extracciónextracted with ethyl acetate
13. 13
    TemperaturaAfter cooling
14. 14
    Extracciónthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate
16. 16
    SecadoThe organic layer was dried over magnesium sulfate
17. 17
    OtroThe solvent was evaporated off under reduced pressure
18. 18
    Otrothe residue was then purified by a silica gel chromatography

Procedimiento

2-[3-(3,4,5-Trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazole-5-carboxylic acid (2.2 g) was added to 1,2-dichloroethane (50 mL). Thionyl chloride (1.0 g) and one drop of N,N-dimethylformamide were added to the mixture, which was then refluxed under heating for 5 hours. After removing the solvent by evaporation, the residues were dissolved in 1,4-dioxane (20 mL), and then added dropwise to the mixture solution comprising water (30 mL), 1,4-dioxane (30 mL), and sodium borohydride (0.5 g) under ice cooling. After the dropwise addition was completed, the reaction solution was refluxed under heating for one hour. After cooling, the reaction solution was poured over ice water, and then extracted with ethyl acetate. After cooling, the extraction was again carried out by adding water and ethyl acetate. The organic layer was dried over magnesium sulfate. The solvent was evaporated off under reduced pressure, and the residue was then purified by a silica gel chromatography to obtain the title compound (1.1 g, 65%).

Fuente