تفاعل #1005954

معادلة التفاعل

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

Thionyl chloride

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title compound

المردود 65.0%

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

المردود 65.0%

المذيبات

1,2-dichloroethane

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةwas then refluxed
2. 2
   درجة الحرارةunder heating for 5 hours
3. 3
   أخرىAfter removing the solvent
4. 4
   أخرىby 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
   درجة الحرارةthe reaction solution was refluxed
9. 9
   درجة الحرارةunder heating for one hour
10. 10
    درجة الحرارةAfter cooling
11. 11
    workup.ADDITIONthe reaction solution was poured over ice water
12. 12
    استخلاصextracted with ethyl acetate
13. 13
    درجة الحرارةAfter cooling
14. 14
    استخلاصthe extraction
15. 15
    workup.ADDITIONby adding water and ethyl acetate
16. 16
    تجفيفThe organic layer was dried over magnesium sulfate
17. 17
    أخرىThe solvent was evaporated off under reduced pressure
18. 18
    أخرىthe residue was then purified by a silica gel chromatography

الإجراء التجريبي

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%).

المصدر