Accordingly the same reaction was tried with o-nitrobenzylamine, prepared by the method of Lellmann and Stickel[(50)], using carbon diselenide[(51)]. The reaction seemed to work, but the mixture formed was difficult to extract and it appeared that other reactions took place at the same time, due to the impurity of the carbon diselenide, as the latter has never been prepared in the pure state.
Another method, which is equally attractive because of its simplicity, is that of Gabriel and Stelzner[(52)],
In accordance with the above reaction o-aminobenzaldehyde should work with equal ease with selenocarbamide, but the initial materials were not available.
The reaction which was used successfully was that of Bogert, Breneman and Hand[(53)],
The hydrogen selenide used in the reaction was prepared from FeSe by the action of hydrochloric acid, or by heating paraffin and selenium, in the proportion of four to one respectively, at 335° to 350°C[(54)].
The selenoquinazoline was prepared from anthranilic nitrile by the following methods—the anthranilic nitrile being prepared from o-nitraniline[(57)],
(a) 20 grams of acetyl-anthranilic nitrile was dissolved in absolute alcohol, and dry hydrogen selenide and dry ammonia passed into the solution for three hours. The quinazoline crystallized out gradually on cooling was filtered out and recrystallized from dilute alcohol. The yield was about ten per cent.