1867.] 



Homologous to Hydrocyanic Acid. 



147 



benzonitrile is not yet perfectly known*. This compound is the well-defined 

 base which some time ago I described as methenyldiphenyldiamine, and 

 which may be looked upon as formed by the association of a molecule of 

 cyanide of phenyl with a molecule of aniline. The successive changes which 

 cyanide of phenyl undergoes when submitted to the influence of water are 

 thus exhibited by the following series of equations : — 



+ 



2H,0 



2 mols. cyanide 

 of phenyl. 



Methenyldi- 

 plienyldiamino . 



Fori 



nd. 



Piienyl- 

 formamide. 



Methenyldi- 

 plienyldiamine. . 



Aniline. 



Phenyl- 

 formamide. 



Aniline. 



A glance at these formulae shows that the metamorphosis of plienylic 

 cyanide is perfectly analogous to that of phenylic cyanate, which I have 

 studied at an earlier date. 



N,0, + 2H,0 == CH^Og 



2 mols. cyanate 

 of phenyl. 



C,3H,,N,0 



Diphenyl-nrea. 



Anhydrous car- 

 bonate of aniline. 



+ H.0 = 



H,0 



Carbonic 

 hydrate. 



- Anhydrous car- 

 bonate of aniline. 



: CH,03 



Carbonic 

 hydrate. 



+ 



+ 



Diphenyl-urea. 



Aniline. 



In conclusion, I may state that I have submitted ethylamine, amylamine, 

 and toluidine to the action of chloroform. The phenomena are, as might 

 have been expected, perfectly analogous. Indeed the application of the 

 new reaction to the different classes of the ammonia derivatives, to the 

 amides, to the diamines and triamines, and perhaps even to some of the na- 

 tural alkaloids, promises a rich harvest of results. Should I have the good 

 fortune of gathering some of these, I shall not fail to present them to the 

 Society, which has so generously encouraged and assisted my earlier re- 

 searches in the field of organic chemistry. 



^ Shortly before his death, Gei'hardt was engaged in expei'iments on the action of 

 pentachloride of phosphorus on the amides, a brief accovmt of which was subsequently 

 published by M. Cahours. Among other substtmces, I find that, by acting with penta- 

 chloride of phosphorus upon benzanilide, Grcrhardt obtained a chloride, Cj3 H^o NCI, 

 which yields with ammonia a crystalline substance. It can scarcely be doubted that this 

 compound is the derivative of benzonitrile corresponding to methenyldiphenyldiamine, 



-HgN^CigHi.N, 4-HCl. 



