Réaction #1005955

Équation de réaction

ammonia water

tetrahydrofuran

methanesulfonyl chloride

tetrahydrofuran

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

tetrahydrofuran

→

title compound

Rendement 45.0%

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

Rendement 45.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   workup.ADDITIONwas added dropwise
2. 2
   workup.ADDITIONAfter the dropwise addition
3. 3
   workup.ADDITIONThe resulting solution was added dropwise to a mixture solution, which
4. 4
   Autrewas separately prepared
5. 5
   workup.STIRRINGAfter stirring the mixture at room temperature for 12 hours
6. 6
   Extractionextracted with ethyl acetate
7. 7
   SéchageThe organic layer was dried over magnesium sulfate
8. 8
   AutreThe solvent was evaporated off under reduced pressure
9. 9
   Autrethe residue was then purified by a silica gel chromatography

Mode opératoire

{2-[3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidin-1-yl]-4-(trifluoro-methyl)-1,3-thiazol-5-yl}methanol (1.05 g) was added to tetrahydrofuran (30 mL). Then, tetrahydrofuran solution (10 mL) comprising methanesulfonyl chloride (0.3 g) was added dropwise thereto under ice cooling. After the dropwise addition was completed, the reaction solution was stirred at room temperature for one hour. The resulting solution was added dropwise to a mixture solution, which was separately prepared to contain 28% ammonia water (50 mL), tetrahydrofuran (100 mL), and methanol (100 mL), under ice cooling. After stirring the mixture at room temperature for 12 hours, the reaction solution was poured over ice water, and then extracted with 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 (0.4 g, 45%).

Source