Reaktion #956398

Reaktionsgleichung

4-methyl-3-nitrobenzoic acid

thionyl chloride

THF

diethylamine

→

N,N-diethyl-4-methyl-3-nitrobenzamide

Lösungsmittel

water

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwas heated
2. 2
   Temperaturunder reflux for 18 hours
3. 3
   SonstigeThe reaction liquid
4. 4
   Einengenwas concentrated under reduced pressure
5. 5
   Sonstigeto give a red-brown oil
6. 6
   workup.ADDITIONwas added under ice cooling
7. 7
   SonstigeThe reaction liquid
8. 8
   Extraktionextracted with ethyl acetate
9. 9
   WaschenThe organic layer was washed with saturated aqueous sodium chloride
10. 10
    Trocknendried over anhydrous sodium sulfate
11. 11
    workup.DISTILLATIONthe solvent was distilled off under reduced pressure

Vorschrift

A mixture of 4-methyl-3-nitrobenzoic acid (1.97 g) and thionyl chloride (6 mL) was heated under reflux for 18 hours. The reaction liquid was concentrated under reduced pressure, followed by an azeotropic process with toluene to give a red-brown oil. To a mixture of the red-brown oil and THF (25 mL), diethylamine (2.6 mL) was added under ice cooling and stirred at room temperature for 5 hours. The reaction liquid was poured into water and extracted with ethyl acetate. The organic layer was washed with saturated aqueous sodium chloride and then dried over anhydrous sodium sulfate, and the solvent was distilled off under reduced pressure to give N,N-diethyl-4-methyl-3-nitrobenzamide (2.61 g) as a brown oil.

Quelle