Reacción #586135

ord-2c5671f66d5d46b186019dbd66010b51

Ecuación de reacción

O
water
COC(=O)c1ccc(-c2c[nH]nc2C(F)(F)F)cc1Cl
methyl 2-chloro-4-(3-trifluoromethylpyrazolyl)benzoate
CCCS
1-propanethiol
O=C([O-])[O-].[K+].[K+]
potassium carbonate
CCCSc1cc(-c2c[nH]nc2C(F)(F)F)ccc1C(=O)OC
methyl 2-propylthio-4-(3-trifluoromethylpyrazolyl)benzoate
Rendimiento 18.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroThe resulting reaction mixture
  2. 2
    Extracciónthe organic matters were extracted with 20 ml of ethyl acetate twice
  3. 3
    Lavadowashed with 30 ml of water twice
  4. 4
    Secadodried over anhydrous magnesium sulfate
  5. 5
    workup.DISTILLATIONthe ethyl acetate was distilled off under reduced pressure
  6. 6
    OtroPurification of the residue by thin layer chromatography

Procedimiento

1.52 g (5.0 mmol) of methyl 2-chloro-4-(3-trifluoromethylpyrazolyl)benzoate, 0.66 g (8.6 mmol) of 1-propanethiol and 0.83 g (6.0 mmol) of potassium carbonate were stirred in 5 ml of N,N-dimethylformamide at 60° C. for 24 hours. The resulting reaction mixture was poured into 50 ml of water, and the organic matters were extracted with 20 ml of ethyl acetate twice. The ethyl acetate layers were combined, washed with 30 ml of water twice and dried over anhydrous magnesium sulfate, and the ethyl acetate was distilled off under reduced pressure. Purification of the residue by thin layer chromatography afforded 0.31 g of methyl 2-propylthio-4-(3-trifluoromethylpyrazolyl)benzoate as a white powder (m.p. 114-116° C.).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US07767626B2uspto-grants-2010_08