Réaction #1005952

ord-24945c868ee545f8bff1fe7849701947

Équation de réaction

CCOC(=O)c1sc(Cl)nc1C(F)(F)F
Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate
FC(F)(F)C1(c2cc(Cl)c(Cl)c(Cl)c2)CCNC1
3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCOC(=O)c1sc(N2CCC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)nc1C(F)(F)F
title compound
Rendement 86.5%
CCOC(=O)c1sc(N2CCC(c3cc(Cl)c(Cl)c(Cl)c3)(C(F)(F)F)C2)nc1C(F)(F)F
ethyl 2-[3-(3,4,5-trichlorophenyl)-3-(trifluoro-methyl)pyrrolidin-1-yl]-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate
Rendement 86.5%

Conditions de réaction

Température
100°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    TempératureAfter cooling
  2. 2
    Extractionextracted with ethyl acetate
  3. 3
    SéchageThe organic layer was dried over magnesium sulfate
  4. 4
    AutreThe solvent was evaporated off under reduced pressure
  5. 5
    Autrethe residue was then purified by a silica gel chromatography

Mode opératoire

Ethyl 2-chloro-4-(trifluoromethyl)-1,3-thiazole-5-carboxylate (1.4 g) [see J. Het. Chem., 22, 1621 (1985)], 3-(3,4,5-trichlorophenyl)-3-(trifluoromethyl)pyrrolidine (1.7 g), and potassium carbonate (0.8 g) were added to N,N-dimethylformamide (50 mL), followed by heating at 100° C. for five hours. After cooling, 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 (2.5 g, 86%).

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09271499B2uspto-grants-2016_03