Reacción #1005952

ord-24945c868ee545f8bff1fe7849701947

Ecuación de reacción

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
Rendimiento 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
Rendimiento 86.5%

Condiciones de reacción

Temperatura
100°CELSIUS
Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    TemperaturaAfter cooling
  2. 2
    Extracciónextracted with ethyl acetate
  3. 3
    SecadoThe organic layer was dried over magnesium sulfate
  4. 4
    OtroThe solvent was evaporated off under reduced pressure
  5. 5
    Otrothe residue was then purified by a silica gel chromatography

Procedimiento

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%).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09271499B2uspto-grants-2016_03