Reacción #1583814

ord-0c546883ac6a4eeb9386a2bcfbc1e624

Ecuación de reacción

OO
hydrogen peroxide
CCc1nc(-c2ccc(F)cc2)c(-c2ccncc2)s1
4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine
CCc1nc(-c2ccc(F)cc2)c(-c2cc[n+]([O-])cc2)s1
desired product
Rendimiento 85.0%
CCc1nc(-c2ccc(F)cc2)c(-c2cc[n+]([O-])cc2)s1
4-[2-Ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine 1-oxide
Rendimiento 85.0%

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    Otrodoes not exceed 15° C.
  2. 2
    Lavadothe organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water
  3. 3
    Secadodried over MgSO4

Procedimiento

3.9 ml (44 mmol) of a 30% strength hydrogen peroxide solution are added dropwise with cooling to a solution of 2.18 g (7.24 mmol) of 4-[2-ethyl-4-(4-fluorophenyl)-1,3-thiazol-5-yl]pyridine and 46.2 mg (0.19 mmol) of methyltrioxorhenium (VII) in 10 ml dichloromethane such that the temperature of the reaction mixture does not exceed 15° C., and the mixture is stirred at room temperature for 16 h. The reaction mixture is then diluted with 100 ml of dichloromethane, and the organic phase is washed successively with 30 ml of a saturated aqueous NaHCO3 solution, 30 ml of a saturated Na2SO3 solution and 30 ml of water and dried over MgSO4. Under reduced pressure, the product is freed from the solvent, giving 1.98 g (85%) of the desired product; 1H-NMR(DMSO-d6) δ: 8.12 (d, 2H), 7.53 (m, 2H), 7.25 (d, 2H), 7.21 (m, 2H), 3.03 (q, 2H), 1.36 (t, 3H).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09198426B2uspto-grants-2015_12