becomes colorless again when the reduction is complete. After all the zinc has disappeared, 1 niol of concentrated nitric acid is added, then 1 mol of benzaldehyde, and the mixture is shaken and scratched to facilitate the separation of the heavy granular precipitate of benzal-aminoguanidine nitrate. The product, recrystallized from water or from alcohol, melts when pure at 100.5°.
Nitroguanidine and nitrosoguanidine both give a blue color with the diphenylamine reagent, and both give the tests described below, but the difference in the physical properties of the substances is such that there is no likelihood of confusing them.
Tests for Nitroguanidine. To 0.01 gram of nitroguanidine in 4 cc. of cold water 2 drops of saturated ferrous ammonium sulfate solution is added, then 1 cc. of 6 N sodium hydroxide solution. The mixture is allowed to stand for 2 minutes, ami is filtered. The filtrate shows a fuchsine color but fades to colorless on standing for half an hour. Larger quantities of nitroguanidine give a stronger and more lasting color.
One-tenth gram of nitroguanidine is treated in a test tube with 5 cc. of water and 1 cc. of 50% acetic acid, and the mixture is warmed at 40-50° until everything is dissolved. One gram of line dust is added, and the mixture is set aside in a beaker of cold water for 15 minutes. After filtering, 1 cc. of 6% copper sulfate solution is added. The solution becomes intensely blue, and, on boiling, gives off gas, becomes turbid, and presently deposits a precipitate of metallic copper. If, instead of the copper sulfate solution, 1 cc. of a saturated solution of silver acetate 12 is added, and the solution is boiled, then a precipitate of metallic silver is formed.
12 Two grams of silver acctate, 2 cc. of glacial acetic acid, diluted to 100 cc., warmed, filtered, and allowed to cool.
Many of the reactions of nitroguanidine, particularly its decomposition by heat and the reactions which occur in aqueous and in sulfuric acid solutions, follow directly from its dearrange-ment. Nitroguanidine dearranges in two modes, as follows.
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