Messrs. Hofmann and Olshausen on Compounds [June 1C, 



b etween this body and the ethylcyanamide, discovered by Messrs. Cahours 

 and Cloez # , which is formed by treating ethylamine with chloride of cya- 

 nogen. The same reagent acting on ethylated water and ethylated am- 

 monia causes in the one case the formation of ethylic cyanate, and in the 

 other that of ethylcyanamide. The close analogy between cyanetholinc 

 and ethylcyanamide, which is, perhaps, best represented by the formula) 



CN(C 2 H 5 )0 and CN(C 2 H 5 )HN, 

 cannot possibly be doubted, and accordingly the easy polymerization of 

 ethylcyanamide, which is readily converted into triethylmelamine, natu- 

 rally raised the question as to whether cyanetholine could not be poly- 

 merized in a similar manner ; in other words, whether there might not 

 exist a series of combinations isomeric with the known cyanuric ethers. 



The experiments undertaken for the solution of this question have been 

 performed in the methyl-, ethyl-, amyl-, and phenyl-series. 



We begin the communication of our observations by a description of the 

 experiments made in the methyl- series ; for although in the first instance 

 we had worked in the ethyl-series, it was the investigation of the methylic 

 compounds which yielded at once results that could not be mistaken. 



Experiments hi the Methyl-series. 



When a stream of gaseous chloride of cyanogen is passed through a 

 dilute solution of sodium methylate in methylic alcohol (we have generally 

 dissolved 20 grms. of sodium in about 400 grms. of anhydrous methylic 

 alcohol), a considerable quantity of common salt is separated. If the cur- 

 rent of gas be continued until the solution smells of chloride of cyanogen, 

 and the excess of methyl alcohol then distilled off, a brown oil remains 

 behind, similar to that which Cloc'z obtained by the corresponding experi- 

 ment in the ethyl-series, and which he described as cyanetholine. This 

 oil sometimes remains fluid for a long time, but generally solidifies on 

 standing. Frequently, however, little or no oil is formed, and when the 

 methyl alcohol is distilled off, there remains a residue which solidifies to a 

 brown crystalline mass. The purification of this substance offers no diffi- 

 culties ; one or two crystallizations from boiling water, in which it is easily 

 soluble, whilst it dissolves but slightly in cold water, and a final treatment 

 with animal charcoal remove the colour. But these crystals, though per- 

 fectly colourless, prove, under the microscope, to be a mixture of two com- 

 pounds, of which the one, crystallizing in fine needles, is the more easily 

 soluble, whilst the other, consisting of rhombic tables, dissolves with 

 greater difficulty. If an intermediate mixed product be sacrificed, they 

 may, by repeated crystallizations from boiling water, be both obtained in 

 a pure state. They are, however, better separated by the extraordinary 

 difference of their solubility in ether, which dissolves the needles and leaves 

 the rhombic tables behind. 



* Ami. Chem. Pkarin. xc. p. 91. 



