OF ARTS AND SCIENCES. 121 



nous white precipitate separates out, which, heated to 100°, goes 

 over with loss of water into mesoxanilide-phenylhydrazone de- 

 scribed below. In this case, therefore, a simple addition of phenyl- 

 hydrazine to the carbonyl group takes place, 



C 6 H 5 N=C° H C 6 H 5 N=C° H /OH 



;co + h 2 n-nh-c 6 h 5 = ;c( 



C 6 H 6 N=C ' CeH^c' X NHNHC 6 H 5 



analogous to the action of ammonia on chloral.* On heating 

 mesoxanilide with acetic anhydride reaction takes place just as in 

 case of chloral, f and a colorless substance crystallizing in needles, 

 and melting at 190° is formed: — 



C 6 H 5 N=C N 

 Mesoxanilide-phenylhydrazone, y C = N-NHC 6 H 5 . 



OH 

 V 



/ 



C 6 H 6 N=Cq 



On adding to a warm alcoholic solution of mesoxanilid-alcoholate 

 one molecule of phenylhydrazine, there is formed almost immedi- 

 ately a voluminous white precipitate, which, filtered off and put on 

 clay plates, is converted into a white powder. This is the hydra- 

 zone alcoholate, 



C 6 H 5 N=C° H .OC 2 H 5 



c 



C 6 H 5 ^C^ H X NHNHC 6 H 5 ; 



so that the reaction between the two substances taken has simply 

 been a splitting off of one molecule of water. In order to convert 

 the substance obtained into the hydrazone, it was heated at 115° 

 to constant weight, which is attained after 10 hours. 



0.1526 gram substance gave 0.3937 gram C0 2 and 0.0729 gram 



H 2 0. 

 0.1532 gram substance gave 20.5 c.c. moist nitrogen at 16° and 



745 mm. 



Theory for C 21 H 18 N 4 2 . Found. 



* Stadeler, Ann. Chem. (Liebig), CVI. 253. 



t V. Meyer and Dulk, Ann. Chem. (Liebig), CLXXI. 73. 



