430 



On the History of the Ethylene Bases. [June 20, 



Action of chloral on ethylenediamine. — In order to become acquainted 

 also with an ethyienediamide belonging to the series of fatty acids, I have 

 prepared the formyl compound. The basic properties of ethylenediamine 

 being, indeed, similar to those of potash and soda, it appeared appropriate 

 to treat the base with chloral in order to produce ethylene diformyldiamide. 

 Experiment has confirmed this anticipation ; the two substances acton one 

 another with great energy, torrents of chloroform being given off which may 

 be readily condensed : on evaporating the residuary liquid on the water- 

 bath, ethylene diformyldiamide remains behind as a transparent syrup. 



(C 2 H 4 )H 4 N 2 + 2[C Cl 3 . CHO] = (C 2 H,)(CHO) 2 H 2 N 2 +2CHCI 3 . 



Both acids and alkalies, especially on boiling, readily change this amide 

 into ethylenediamine and formic acid. In passing I may mention that 

 chloral may also be conveniently used for the preparation of other 

 formamides. When anhydrous ethylamine and chloral are brought to- 

 gether, a white crystalline mass is immediately formed by the direct union 

 of the two substances. This, on distillation, gives considerable quantities 

 of pure ethylformamide boiling at 199°, chloroform being eliminated at the 

 same time. 



Formamide also may be obtained in this manner, but less advantageously. 



Action of oxalic ether on ethylenediamine. — If a concentrated alcoholic 

 solution of ethylenediamine be mixed with oxalic ether, the liquid becomes 

 warm and solidifies after a few minutes to a white amorphous mass, which is 

 almost insoluble both in water and in alcohol. On evaporating the alcoholic 

 filtrate from the insoluble body on the water-bath, a white crystalline sub- 

 stance is left, which is soluble both in water and in alcohol. 



The white amorphous substance is swollen up like starch-paste, and can 

 only be washed with difficulty ; moreover, as no solvent for it was to be 

 found, it could not be further purified, a circumstance which was not with- 

 out a slight influence on the analytical results. As might be expected, the 

 amorphous body is ethylene oxamide, 



C S H 4 ] 

 Q,H t N I 0,= C,0, N 2 . 



hJ 



The substance crystallizing in white scales, which is obtained on evapo- 

 rating the filtrate from ethylene oxamide, was found on analysis to be 

 ethylic ethylene oxamate : 



C H NoJ^WW^lo 



The action of ethylenediamine on oxalic ether is thus seen to be pre- 

 cisely what theoretically might be expected. 



