134 PROCEEDINGS OP THE AMERICAN ACADEMY 



scopic, has a strong acid smell like an acid haloid, and is in- 

 stantly decomposed by water or alcohol with marked evolution of 

 heat. The salt dissolves in chloroform, but is insoluble in ether 

 and ligroine. Its behavior towards water and alkalies was carefully 

 studied. 16 grams were added slowly to 300 c.c. sodic hydrate 

 (1:10) kept at 0° by means of ice. Reaction instantly takes place, 

 and a portion goes into solution, another remains as a sticky gray- 

 ish mass. The mixture is immediately extracted with ether, and, 

 to get rid of any diphenylformamidine taken up by the ether, 

 washed with dilute hydrochloric acid. The ethereal solution is 

 then washed with soda, and dried with calcic chloride. After 

 distilling off the ether, 3 grams of an oily residue were obtained, 

 consisting chiefly of formanilide. On adding ligroine and cooling, 

 the formanilide solidified (2 grams), and recrystallized from a mix- 

 ture of ligroine and ether was obtained pure (mpt. 48°). 



The above mentioned hydrochloric acid extract, as well as some 

 residue not extracted by the ether in the first place, contains diphe- 

 nylformamidine (mpt. 138°). 1.5 grams were obtained. 



In an experiment where 15.8 grams phenylimidoformylchloride 

 salt and 180 c.c. of water were taken, and the experiment other- 

 wise carried out as above with sodic hydrate, 2 grams of formani- 

 lide and .4 gram diphenylformamidine were obtained. 



The formation of diphenylformamidine in the two cases above 

 is easily explained by considering that aniline is split off; and, in 

 fact, the presence of aniline, as well as that of formic acid, in both 

 reactions was proved. 



Gautier* also obtained, by treating methyl- and ethylisocyanide 

 with dry hydrogen chloride, salt-like products of the general for- 

 mula 2 KNC, 3HC1. He further found that they are instantly 

 decomposed by water and caustic potash, giving methyl- and ethyl- 

 formiamide respectively 



.OH , OH 



CH 3 N=C; and GJLN<r 



X H X H 



as chief products. 



These experiments are sufficient to prove that the isonitriles 

 react with hydrogen chloride giving hydrochlorides of alkylimide- 

 formylchlorides, 



2RN=C^, HC1. 

 * Loc. cit., XVII. 223 and 240. 



