Reaktion #350761

Reaktionsgleichung

4-(4-chloro-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole

morpholine

dimethyl sulfoxide

→

4-(4-morpholino-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole

Ausbeute 91.5%

Lösungsmittel

dimethylformamide

Reaktionsbedingungen

Aufarbeitung

1. 1
   Temperaturwith heating
2. 2
   workup.DISTILLATIONThe reaction mixture was subjected to vacuum distillation
3. 3
   workup.ADDITIONThe residue was added to ice water
4. 4
   workup.ADDITIONan aqueous sodium hydrogencarbonate solution was added
5. 5
   ExtraktionThe solution was extracted with dichloromethane three times
6. 6
   ExtraktionThe combined extract
7. 7
   Waschenwas washed with an aqueous sodium chloride solution
8. 8
   Trocknendried over magnesium sulfate
9. 9
   SonstigeThe solvent was removed by distillation
10. 10
    SonstigeThe residue was purified by silica gel column chromatography
11. 11
    Sonstigerecrystallized from ethyl acetate-n-hexane

Vorschrift

A solution of 1 g of 4-(4-chloro-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole and 636 mg of morpholine dissolved in 20 ml of dimethylformamide and 20 ml of dimethyl sulfoxide was refluxed at 150° C. for 2-3.5 hours with heating. The reaction mixture was subjected to vacuum distillation. The residue was added to ice water, and an aqueous sodium hydrogencarbonate solution was added. The solution was extracted with dichloromethane three times. The combined extract was washed with an aqueous sodium chloride solution and dried over magnesium sulfate. The solvent was removed by distillation. The residue was purified by silica gel column chromatography and recrystallized from ethyl acetate-n-hexane to obtain 1.03 g of 4-(4-morpholino-3-nitrophenyl)-2-(3,4-diethoxyphenyl)thiazole.

Quelle