Reacción #58925

Ecuación de reacción

2-(4-nitrophenyl)acetohydrazide

ethyl chlorocarbonate

diphosphorus pentaoxide

hexamethyldisiloxane

→

5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one

Rendimiento 51.2%

Disolventes

Water

N,N-dimethylacetamide

1,2-dichlorobenzene

Water

Condiciones de reacción

Tratamiento posterior

1. 1
   Extracciónthe mixture was extracted with ethyl acetate
2. 2
   LavadoThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
3. 3
   Secadodried over anhydrous magnesium sulfate
4. 4
   Concentraciónconcentrated
5. 5
   Otroto give colorless crystals
6. 6
   workup.STIRRINGwas stirred at 160° C. for 2 hrs
7. 7
   Extracciónthe mixture was extracted with ethyl acetate
8. 8
   LavadoThe organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine
9. 9
   Secadodried over anhydrous magnesium sulfate
10. 10
    Concentraciónconcentrated

Procedimiento

A mixture of 2-(4-nitrophenyl)acetohydrazide (0.50 g), ethyl chlorocarbonate (0.34 g) and N,N-dimethylacetamide (10 mL) was stirred at room temperature for 1 hr. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give colorless crystals. A mixture of the obtained crystals, diphosphorus pentaoxide (1.50 g), hexamethyldisiloxane (2.96 g) and 1,2-dichlorobenzene (10 mL) was stirred at 160° C. for 2 hrs. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The organic layer was washed successively with saturated aqueous sodium hydrogen carbonate and saturated brine, dried over anhydrous magnesium sulfate, and concentrated to give 5-(4-nitrobenzyl)-1,3,4-oxadiazol-2(3H)-one as pale-yellow crystals (0.29 g, yield 50%). Recrystallization thereof from ethyl acetate-hexane gave pale-yellow prism crystals. melting point: 170-171° C.

Fuente