Synthesis of 2-methyl-4-selenoquinazolone, 2-phenylbenzoselenazole, and its derivatives / Dissertation submitted in partial fulfillment of the requirements for the degree of Doctor of Philosophy in the Faculty of Pure Science of Columbia University

by Yü-Gwan Chen

An Azo Dye

Five and four tenth grams of the monoamino compound were dissolved in hot conc. HCl, cooled in ice, and diazotized with sodium nitrite solution, until starch iodide paper showed excess nitrous acid. The diazotization was performed in ice, with mechanical stirring, and required about an hour. The diazo solution was poured into a solution of 3 grams B-naphthol in 8 grams of NaOH and 60 cc. of water, while gradually stirring. A very deep red solution formed. This was acidified with excess HCl, salted out by NaCl, and crystallized from aniline-alcohol mixture. In the pure state, it is a deep red powder, with a metallic lustre when rubbed, melting at 284.2°C. An analysis showed the following result,

	Calculated for C23H15N3OSe	Found
Nitrogen	9.81%	9.75%