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

Mononitro Derivative

The mononitro derivative of the selenazole, 6-nitro-2-phenylbenzoselenazole, was prepared by nitration with nitric acid at a low temperature:

Twenty-five grams of the selenazole were dissolved in 150 grams of concentrated sulphuric acid, keeping the temperature below the room temperature until complete solution took place. It was then cooled on a freezing mixture and a mixture of sulphuric and nitric acids (previously prepared and cooled by mixing 9.5 grams of nitric and fifteen grams of sulphuric acids) slowly dropped into it in the course of half an hour, using mechanical stirring for four hours. The solution was then poured into two liters of water (ice water), filtered, dried, and recrystallized from acetic acid, and alcohol with the help of animal charcoal. The yield was 95 per cent.

This nitro compound crystallizes in flattened needles of a light yellow color. It melts at 202.4°C. (corr.). It is very insoluble in water; but soluble in hot acetic acid, acetic anhydride, nitrobenzene, nitrotoluene, toluene, benzene, alcohol, and difficultly soluble when cold. The crystals were analyzed and gave the following results,

	Calculated for C13H8N2O2Se	Found
		I	II
Nitrogen	9.24%	9.36%	9.48%