Dimethylformamide → 4-(4-Pyridinylamino)benzamide
Reaktionsgleichung
[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12](O)=[O:13])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1.S(Cl)(Cl)=O.C[N:22](C)C=O>>[N:1]1[CH:6]=[CH:5][C:4]([NH:7][C:8]2[CH:16]=[CH:15][C:11]([C:12]([NH2:22])=[O:13])=[CH:10][CH:9]=2)=[CH:3][CH:2]=1Komponenten
4
Reaktionsbedingungen
- Temperatur
- 0 °C
Versuchsvorschrift
4-(4-Pyridinylamino)benzoic acid (43 g), 400 ml of thionyl chloride and 0.4 ml of dimethylformamide were mixed at 0° C. The mixture was heated on a steam bath for about 19 hours. The excess thionyl chloride was removed under reduced pressure and the residue azeotroped twice with toluene. The resulting acid chloride was suspended in 300 ml of acetonitrile. The suspension was cooled to 0° C. and an ice-cold solution of 0.8 ml of ammonia in 250 ml of acetonitrile was added dropwise over a period of 20 minutes. The reaction mixture was stirred for four hours and the solid material collected by filtration. The latter was slurried in 1 liter of water and 25 ml of saturated aqueous potassium carbonate was added. The solid product was collected and recrystallized twice from methanol to give 22 g of 4-(4-pyridinylamino)benzamide, m.p. 223°-226° C. A further recrystallization gave a sample with the m.p. 225.5°-227.5° C.