128 PROCEEDINGS OF THE AMERICAN ACADEMY 



16 grams of pyruvic-anilidimideehloride, for example, were di- 

 vided into two parts, and treated simultaneously as follows. 



a. 8.3 grams were slowly poured into 200 c.c. of sodic hydrate 

 (1 : 10), which was kept at 0° by means of ice. A strong smell of 

 isonitrile is noticed immediately. After standing for an hour, 

 during which the mass was kept well stirred, it was extracted with 

 ether. The ether was then distilled off, and the residue distilled 

 with steam, the distillate thereupon extracted with ether, and, in 

 order to remove any aniline possibly formed, treated with dilute 

 sulphuric acid. After drying the ether solution with solid caustic 

 potash, there was left, after getting rid of the ether, 2.4 grams of 

 oil, which was practically pure phenylisocyanide. 



b. 1.1 grams poured slowly into 110 c.c. of ice water solidified 

 quickly, and not a trace of phenylisocyanide was noticed. From 

 the solid mass 4 grams of pure pyruvic anilide (see below), were 

 obtained. 



The same noteworthy difference in behavior towards water 

 and alkalies is also shown by mesoxanilidimidechloride (described 

 above). Whereas water converts it into mesoxanilidehydrate, 

 and not a trace of phenylisocyanide is observed, on pouring the 

 substance into dilute sodic hydrate (1:10), very much phenylisocy- 

 anide results. In an experiment carried out as above under a, 

 1 gram isonitrile was obtained from 4 grams of imidechloride. 



This substance is therefore also split in two ways, according to 

 the conditions : — 



1. With water, 



C 6 H 5 N</ C 6 H 5 N=c£ H OH 



^CO + 3H 2 = ;CX5 + 2HC1. 



C 6 H 8 N=C^j C 6 H 5 N=C ( 3 H UM 



2. With alkalies, 



P TT "N"=p 



J ) CO + 2 H 2 = 2 C 6 H 5 N=C= + C0 2 + H 2 + 2 HC1. 

 C 6 HVN"=Cqj 



This is, however, not at all a behavior peculiar to the two cases 

 mentioned, but seems to be a very general property of imidechlo- 



