Reacción #158287

Ecuación de reacción

N′-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide

carbon tetrachloride

triphenylphosphine

→

title compound

Rendimiento 53.8%

2-(3,4-difluorobenzyl)-5-[3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)phenyl]-1,3,4-oxadiazole

Rendimiento 53.8%

Disolventes

acetonitrile

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturato cool to room temperature
2. 2
   Filtraciónthe precipitate was filtered off
3. 3
   Concentraciónthe filtrate was concentrated
4. 4
   workup.ADDITIONWater was added to the residue
5. 5
   Extracciónthe mixture was extracted with ethyl acetate
6. 6
   SecadoThe extract was dried over anhydrous magnesium sulfate
7. 7
   Otrothe solvent was evaporated under reduced pressure
8. 8
   OtroThe residue was purified by silica gel column chromatography (ethyl acetate)
9. 9
   workup.ADDITIONEthyl acetate was added to the
10. 10
    Otroobtained crude product
11. 11
    Filtraciónthe precipitate was filtered off
12. 12
    Concentraciónthe filtrate was concentrated
13. 13
    workup.ADDITIONAcetonitrile was added to the obtained residue
14. 14
    Filtraciónthe resultant precipitate was collected by filtration

Procedimiento

A mixture of N′-[(3,4-difluorophenyl)acetyl]-3-methoxy-4-(2-methyl-1,3-oxazol-5-yl)benzohydrazide (4.69 g), carbon tetrachloride (2.24 mL) and triphenylphosphine (12.3 g) in acetonitrile (117 mL) was stirred at 80° C. for 2 hr. The mixture was allowed to cool to room temperature, the precipitate was filtered off, and the filtrate was concentrated. Water was added to the residue, and the mixture was extracted with ethyl acetate. The extract was dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (ethyl acetate). Ethyl acetate was added to the obtained crude product, the precipitate was filtered off, and the filtrate was concentrated. Acetonitrile was added to the obtained residue, and the resultant precipitate was collected by filtration to give the title compound (2.41 g).

Fuente