Aniline → N,N,N'-triphenyl-4-phenylenediamine

Beteiligte Stoffe

Reaktionsschritte

In a two-neck round bottom flask, (4-bromo-phenyl)-diphenyl-amine (12 g, 0.037 mol), aniline (16.26 ml, 0.178 mol), BINAP (0.4 g, 3% mol), Pd(OAc)2 (7.4 g, 4% mol), and NaOtBu (17.2 g, 0.178 mol) are dissolved in toluene (300 mL), and then are maintained for 18 hours by reflux. On completion of the reaction, the flask having the resultant solution is cooled, and then toluene, a solvent of the reaction, is removed from the resultant solution. After that, the resultant solution having no toluene reacts on methylene-chloride and water, and then methylene-chloride is removed therefrom, and is performed by silica gel column chromatography with a solvent of methylene-chloride and hexane at a ratio of 2 to 1. After that, the solvent is removed from the resultant solution of completing silica gel column chromatography, and is recrystallized and filtered with methylene-chloride and petroleum ether, thereby obtaining a white solid, N,N,N′-triphenyl-benzene-1,4-diamine (11.0 g, 88%).

Herkunft & Nachweise