Monoamino Derivative
The conversion of mononitro compound to 6-amino-2-phenylbenzoselenazole was accomplished by the action of tin and hydrochloric acid as follows:
30.3 grams of nitro compound were mixed with 42 grams of twenty mesh tin in a liter flask, immersing the latter in cold water. 175 cc. of conc. HCl were slowly added to the flask. In some cases it was necessary to apply initial heating but when once the reaction started it took place rapidly. After the effervescence had abated, the flask was heated over a free flame, under a return condenser, for two hours. The solution usually turned to a pasty mass, due to the formation of a tin double salt. The mixture was dissolved in a large volume of water and heated on a water-bath, the precipitate filtered out, washed, and preserved. The clear filtrate was treated with concentrated alkali, in excess, the separated amine collected, washed with water, dried and recrystallized from alcohol, using bone-black. The precipitate set aside was treated with strong alkali, the insoluble residue washed, recrystallized, and added to the main product. The yield was 75 per cent.
This amine crystallizes from alcohol in fine yellowish needles, melting at 201.2°-202.3°C (corr.). It is insoluble in water and ether, difficultly soluble in the hot; and fairly soluble in aniline. A pure sample was analyzed and gave the following results:
| Calculated for C13H10N2Se | Found | ||
|---|---|---|---|
| I | II | ||
| Nitrogen | 10.25% | 10.34% | 10.42% |
| Carbon | 57.18 | 57.17 | 57.00 |
| Hydrogen | 3.69 | 3.79 | 3.85 |