NEF. — BIVALENT CARBON. 173 



always takes place on recrystallizing the substance from water. Phe- 

 nylisuretine shows altogether a great tendency to decompose in this 

 manner. On melting the solid substance, a strong smell of phenyl- 

 isocyanide is noticed ; also on warming with sodic hydrate, in which 

 it first dissolves. The compound possesses strong basic properties, 

 and dissolves immediately in cold dilute acids. It gives a deep purple 

 red coloration with ferric chloride, and reduces silver solutions on 

 warming. Because of its decomj)osition into phenylisocyanide, the 

 substance burns with great difficulty.* 



0.1435 gram substance, dried over H2SO4 in a vacuum, gave 0.3202 



gram CO2 and 0.0799 gram HgO. 

 0.1549 gram substance, dried over H2SO4 in a vacuum, gave 0.3452 



gram CO2 and 0.0848 gram HgO. 

 0.1526 gram substance, dried over HjSO^ in a vacuum, gave 0.3428 



gram CO2 and 0.0843 gram H2O. 

 0.1544 gram substance gave 28.5 c.cm. N, at 20° and 755 mm. 



Theory for C,Il8N„0. 



C 61.76 



H 5.89 



N 20.59 



In order to prove absolutely that the substance was really phenyl- 

 isuretine it was necessary to obtain it synthetically from a formic 

 acid derivative. To effect this, two ways were open ; the substance 

 could, in the first place, easily be formed from phenylisocyanide and 

 hydroxylamine, by addition, 



C,H,N : C + H2NOH = C,H,N : C ^jjQjj 



In the second place, it could probably easily be obtained from isuretine 

 by means of aniline hydrochloride. 



The second method was first chosen, and since this succeeded 

 directly and quantitatively, the first way, which m all probability 

 would also yield phenylisuretine, was not tried. 



Preparation of Isuretine, HN : C TVTTjfvTT • — Lossen and Schiffer- 



decker have obtained this compound from prussic acid and hydroxyl- 

 amine.f The following slight modification of their method gives a 

 very good yield of isuretine. A solution of 30 grams of cyanide of 



* Ann. Cliem. (Liebig), CCLXX. 276. 

 t Ibid., CLXVI 295. 



