The Synthesis of Certain Substituted Sym-Diphenylcarbazides

Abstract

It is perhaps advisable here to give a complete resume of the reactions involved in these syntheses. In all cases, a substituted aniline was the starting product which was diazotized with NaN02 in acid solution at a temperature maintained between 0 degrees and 5 degrees C. The diazo compound was then reduced, either with Na2S204, Zn and HAc, Na2S03, or SnCl2 [not used in the experiments carried out in this thesis]. The products obtained are extremely impure and very water soluble; thus their further purification is the major problem to overcome. Little success is obtained in the general method tor recystallization; therefore the method using the reflux condenser was applied with moderate success. Yields are not high to begin with, and decrease rapidly on several recrystallizations. As for actual formation of the substituted diphenylcarbazides, those bearing the sulfonyl group seemed the easiest to make and the hydroxy derivatives by far the most difficult. In closing, it may be said tha:t the possibility of preparing the substituted diphenylcarbazides is good, and with the proper amount of care and patience, it should not be too difficult to get several. These could be used further to investigate the cadmium ion, in water solution, and perhaps solve some of the difficulties that arise :from such interfering cations as zinc and so forth. Time and patience are the only real drawback in their ultimate synthesis. [From Summary]