110 PROCEEDINGS OF THE AMERICAN ACADEMY 



Found. 



II. 



13.84 



Phenylisocyanide is lighter than water, specific gravity 0.977 at 

 15° (Westphal). It possesses a horrible smell, a bitter taste, and 

 causes headaches and flow of the saliva. Continued inhalation of 

 its vapors produces nausea, and nervous exhaustion.* 



Nascent hydrogen converts it into mononiethylaniline : 10 grams 

 were dissolved in 90 grams amylalcohol, 6 grams of sodium added, 

 and the mixture heated to boiling until the sodium had disap- 

 peared. The smell of isocyanide was no longer present, and after 

 washing the amylalcohol with water it was treated with dilute 

 hydrochloric acid, and the acid solution evaporated one half on a 

 water bath, and then made alkaline : the oil which separates out was 

 extracted with ether, and dried with anhydrous sulphate of copper. 

 On fractional distillation, 7 c.c. of an oil, boiling from 187°- 

 191°, were obtained, which treated in acid solution with sodic 

 nitrite gave the well known methylaniline nitroseamine. This 

 was converted back again by means of tin and hydrochloric acid 

 into mononiethylaniline (bpt. 189°-192°); the latter substance 

 finally treated with acetic anhydride, and thus 4 grams of methyl- 

 acetanilide (mpt. 99°) were obtained. These reactions were so 

 conclusive that an analysis of the mononiethylaniline was consid- 

 ered superfluous. 



Gautierf has shown that methyl- and ethyl-isocyanide react with 

 acetic acid as follows : 



,COCH 3 



HOCOCH, -o^t_^ H ^/ 



CO-CH 3 



EiW + H6COCH3 = EN=C OH + °n 



Alkyl Formamide. 



Phenylisocyanide reacts with acetic acid (2 molecules) slowly at 

 ordinary temperature, forming acetic anhydride and formanilide, 



C 6 H 5 N=Cqtt 



* Gautier states, loc. cit., XVII. 218, that methyl and ethylisocyanicle are 

 not really to be regarded as poisonous substances, since several drops of either 

 when put in the eyes or mouth of a dog had absolutely no effect, and even 

 0.5 gram put on an open wound produced no apparent effect. He states, how- 

 ever, that they have a marked effect on the human system. 



t Loc. cit., XVII. 223 and 241. 



