OF ARTS AND SCIENCES. 119 



Mesoxanilide and its Derivatives. 



Mesoxanilid-alcoholate = Monoethylether of Dloxymalonic Anilide, 



C 6 H 5 N=C Xc , OH 

 CeH^C 7 0C2Hs 



Mesoxanilidimidecliloricle takes up water slowly from the air 

 and becomes solid. On pouring a large amount of water over the 

 oil, and stirring with a glass rod, all at once reaction sets in, with 

 marked evolution of heat, and the mass solidifies; in order to de- 

 compose mechanically enclosed material, it is converted by means of 

 a pestle into a fine powder. The grayish white residue consists of 

 almost pure mesoxanilidehydrate, and equals in weight the phenyl- 

 isocyanide taken in the first place. It was generally made directly 

 from the crude, not distilled mesoxanilidimidechloride. In order 

 to purify this, it was recrystallized twice from boiling alcohol, 

 which converts the hydrate into the alcoholate. 



0.1686 gram substance dried over H 2 S0 4 in vacuum gave 0.4077 



gram C0 2 and 0.0896 gram H 2 0. 

 0.2074 gram substance gave 16.7 c.c. moist nitrogen at 16° and 



742 mm. 



Theory for C 17 H ]8 N 2 4 . Found. 



C 64.97 65.94 



H 5.73 5.90 



N 8.92 9.11 



Mesoxanilid-alcoholate is readily soluble in hot, but only slightly 

 so in cold alcohol, and crystallizes out in colorless silky needles. 

 On heating it in a capillary tube it begins to get yellow at 100°, 

 and melts with gas evolution (alcohol) at 145° to 151°, according as 

 the temperature is raised slowly or quickly. In boiling alcoholic 

 or benzine solution, the alcoholate dissociates to a marked extent, 

 and the solutions are colored pure yellow, but on cooling, already 

 at 50° they become colorless. This explains why in the above 

 analysis the per cent of carbon found was somewhat high. The 

 alcoholate dissolves in dilute sodic hydrate and slightly in hot 

 water whereby, however, it is converted into mesoxanilidehydrate. 



