Reacción #1944451

Ecuación de reacción

sodium hydrogen carbonate

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline

triphosgene

2,4,5-Trifluoroaniline

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title compound

Rendimiento 73.2%

N-(2,4,5-Trifluorophenyl)-N'-{4-[(6,7-dimethoxy-4-quinolyl)oxy]phenyl}urea

Rendimiento 73.2%

Disolventes

toluene

triethylamine

Condiciones de reacción

Tratamiento posterior

1. 1
   Temperaturawith heat
2. 2
   workup.ADDITIONwas added
3. 3
   Temperaturathe admixture was refluxed
4. 4
   Temperaturawith heat for 3 minutes
5. 5
   Temperaturathe admixture was refluxed
6. 6
   Temperaturawith heat for 20 minutes
7. 7
   Extracciónthe reaction mixture was extracted 2 times with ethyl acetate
8. 8
   Lavadothe organic layer was then washed with brine
9. 9
   Secadodried with anhydrous sodium sulfate
10. 10
    OtroThe solvent was removed by reduced-pressure distillation
11. 11
    Otrothe resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1)

Procedimiento

6,7-Dimethoxy-4-(4-aminophenoxy)quinoline (50 mg) was dissolved in toluene (5 ml) with heat, after the addition of triethylamine (1 ml), triphosgene (55 mg) was added, and the admixture was refluxed with heat for 3 minutes. 2,4,5-Trifluoroaniline (75 mg) was added to the reaction mixture, and the admixture was refluxed with heat for 20 minutes. After the addition of aqueous sodium hydrogen carbonate, the reaction mixture was extracted 2 times with ethyl acetate, and the organic layer was then washed with brine and dried with anhydrous sodium sulfate. The solvent was removed by reduced-pressure distillation, and the resulting residue was purified by column chromatography on silica gel eluting with chloroform/acetone (10/1) to obtain 58 mg of the title compound (yield: 73%).

Fuente