Reaktion #84322

Reaktionsgleichung

N-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide

N,N-dimethylformamide water

sodium nitrite

→

desired product

Ausbeute 43.9%

N-[2-(3,5-dichloropyridin-2-yl)-2-(hydroxyimino)ethyl]-2-(trifluoromethyl)benzamide

Ausbeute 43.9%

Lösungsmittel

—

mixture

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   SonstigeAfter completion of the reaction
2. 2
   Temperaturto cool to room temperature
3. 3
   Extraktionextracted with ethyl acetate (100 ml×2)
4. 4
   Waschenwashed with water (50 ml×1)
5. 5
   Trocknendried over saturated aqueous sodium chloride
6. 6
   Sonstigeanhydrous sodium sulfate, and the solvent was evaporated under reduced pressure
7. 7
   SonstigeThe resulting residue was purified by silica gel column chromatography

Vorschrift

To 14.00 g of N-[2-(3,5-dichloropyridin-2-yl)-2-nitroethyl]-2-(trifluoromethyl)benzamide in 70 ml of a mixture of N,N-dimethylformamide-water (7:1), 16.62 g of sodium nitrite was added, and the mixture was stirred at 60° C. for 18 hours. After completion of the reaction, the reaction mixture was allowed to cool to room temperature, poured into 100 ml of water and extracted with ethyl acetate (100 ml×2). The resulting organic layers were combined, washed with water (50 ml×1) and dried over saturated aqueous sodium chloride and then anhydrous sodium sulfate, and the solvent was evaporated under reduced pressure. The resulting residue was purified by silica gel column chromatography using ethyl acetate-hexane (with a gradient of from 3:7 to 1:1) as the eluent to obtain 5.90 g of the desired product as pale yellow crystals.

Quelle