82 KANSAS UNIVERSITY QUARTERLY. 



gave such good results that, by analogy, it might have been expected 

 that the method would be general in its application. The yield of 

 amid in each case was quantitative ; and they were, moreover, pure 

 and well crystallized, yet, with the exception of cyanacetic ethyl ester, 

 no others have given as good results. 



The reaction, too, was much less violent than the one accompany- 

 ing the formation of the amids from the chlorids. The esters and the 

 ammonia mix with little rise in the temperature of the ammonia. 



Cyanacetic ethyl ester gave a well-crystallized body which melted 

 at 118°, agreeing with the melting-point of the substance given by 

 Henry (Bl. 48, 656), but differing from that assigned by Hoff 105° 

 (J. 1864,561). 



The ethyl esters of the fatty acids were tried, as follows : Formic, 

 acetic, propionic, butyric, valeric, caprylic, and pelargonio. None of 

 these yielded amids except pelargonic acid ethyl ester, which gave 

 crystals mixed largely with the unchanged ester. When these crys- 

 tals were freed from the ester, they gave a melting-point of 99^ agree- 

 ing with that given by Hofmann (B. 15, 984). 



From the results above described, it seemed probable that the sub- 

 stitution of one or more hydrogen atoms in the alkyl radical of the acid 

 by the halogen had some influence upon the readiness with which an 

 amid could be formed. To test this hypothesis, the action of am- 

 monia on the esters of a number of substituted fatty acids was inves- 

 tigated, with the result that we have thus far obtained amids from 

 only two of them, dibromacetic ethyl ester and chlorpropionic ethyl 

 ester. Substances were obtained from these whose melting-points 

 correspond to those recorded in chemical literature. From some 

 of the others crystalline products were obtained, but the melting-points 

 varied from those recorded for the expected amids. For instance, 

 from the bromacetic ethyl ester a mass of white cubical crystals was 

 formed, which did not melt below 200°, which sublimed at high tem- 

 peratures, and which turned red on being heated or after standing a 

 a few days. This substance seems to be a mixture of ammonium bro* 

 mid and some other compound, which we have not yet separated 

 and identified, but which is possibly glycinamid or amidoacetamid. 

 From tribromacetic acid ethyl ester white crystals were obtained 

 which melted at 45° instead of 120°, the temperature at which tribro- 

 macetamid should melt ( Brezina, J. 1881, 673). The composition of 

 this substance has not yet been determined. Bromin substitution 

 products of esters of some of the higher fatty acids give solid resi- 

 dues resembling that obtained from bromacetic acid ester and proba- 

 bly consisting of ammonium bromid and decomposition products. 



The only chlorin substitution product besides the chloracetic 



