Reaktion #1005952

ord-24945c868ee545f8bff1fe7849701947

Reaktionsgleichung

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
Ausbeute 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
Ausbeute 86.5%

Lösungsmittel

Reaktionsbedingungen

Temperatur
100°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    TemperaturAfter cooling
  2. 2
    Extraktionextracted with ethyl acetate
  3. 3
    TrocknenThe organic layer was dried over magnesium sulfate
  4. 4
    SonstigeThe solvent was evaporated off under reduced pressure
  5. 5
    Sonstigethe residue was then purified by a silica gel chromatography

Vorschrift

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%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09271499B2uspto-grants-2016_03