OF ARTS AND SCIENCES. 129 



rides. Wallach and his co-workers * have often noticed, in their 

 work on this class of substances, that on pouring amide and imide 

 chlorides into sodic hydrate, a strong smell of isonitrile appeared. 

 The amount formed was never determined, and they were unable 

 to offer an explanation for its formation; its appearance was sup- 

 posed to be due to the presence of some unknown impurity. 



The above results make it probable that a new method for mak- 

 ing isonitriles is accessible through the alkylated acid amides, 



.OH 



r-c; 



^NR 



and phosphorus pentachloride. Up to the present time, however, 

 no further experiments have been carried out in this direction. 



C 6 H 5 N=C OH 



Pyruvic Anilide, I 



CH 3 -CO 



In order to prepare this substance, it is not necessary to start 

 with pure distilled pyruvic-anilidimidechloride. The crude pro- 

 duct obtained by heating phenyl isocyanide and acetylchloride is 

 poured into a large amount of water, and in a short time the oil 

 solidifies, with marked evolution of heat. The mass is ground 

 to a fine powder, filtered off, and then crystallized once from boil- 

 ing water. Recrystallized once more from alcohol, a perfectly 

 colorless product is obtained, melting at 104°. The yield equals 

 generally in weight that of the isonitrile applied. 



0.1697 gram substance dried over H 2 S0 4 in vacuum gave 0.4120 

 gram C0 2 and 0.0854 gram H 2 0. 



* Wallach, Ann. Chem. (Liebig), CLXXXIV. 75 and 75; in the case of 



CI 

 C 2 H 5 N=C( 



CO2C0H5 



Wallach, Ann. Chem. (Liebig), CCXIV. 226; in the case of 



.CI 



CCI3 

 Klinger, Ann. Chem. (Liebig), CLXXXIV. 270, 276, 279, and 283 ; in the case of 



C 2 H 6 N=cC 



CI /y C\. 2 



C 6 H 5 N=CC and C G H 5 NH Cf 



X C0 2 C 2 H 5 V C0 2 C 2 H 5 . 



VOL. XXVII. (n. S. XIX.) 9 



