172 PROCEEDINGS OF THE AMERICAN ACADEMY. 



2. From formylchloridoxime : 



g ) C : NOH + 2AgN03 = C : NOAg + AgCl + 2 HNO3. 



3. From formylsulphate-oxime : 



HON : CQgQ Qjj + SAgNOg = C : NOAg + Ag2S04 + 3 HNO3. 



4. From thioformhydroxamic acid : 



HON : Cgpj + SAgNOs = C : NOAg + AgsS + HNO3. 



Behavior of Formylchloridoxime towards Aniline. 



The constitufion of formylchloridoxime is proved by the fact that 

 aniline coverts it quantitatively into phenylisuretine, according to the 

 reaction ; 



NHCeHs 



HON: C^j + 2C6H5NH2 = HONH-C-Cl + CeH^NHa 



H 



Addition Product. 



= ^^^J^)C:NC6H5 + C6H5NH3CI. 



Phenylisuretine 



On adding: an ethereal solution of aniline (2 molecules, 12.5 grams) 

 to a concentrated ethereal solution of formylchloridoxime (obtained 

 from 12 grams silver fulminate), a clear solution at first takes place, 

 but very soon a white salt begins to separate out in large quantity. 

 After standing for one hour, much ether is added, and the salt filtered 

 off. The residue, 9.2 grams, consists of a mixture of aniline hydro- 

 chloride and phenylisuretine, which, since the latter substance is insol- 

 uble in cold water, can readily be separated. The ethereal filtrate 

 gives, on evaporation, phenylisuretine and traces of aniline. Alto- 

 gether 6.5 grams of phenylisuretine were obtained. It is purified by 

 crystallizing from ether, and obtained in flat colorless needles, melting 

 with decomposition at 138°. The substance crystallizes from water in 

 long fibrous colorless needles, or, if the solution is dilute, in leaflets. 

 A slight decomposition into phenylisocyanide and hydroxylamine, 

 according to the equation, 



CeH.N : C^^LOR = ^«"=^ '' ^ + H.,NOH, 



