290 
CHEMISTRY: JOHNSON, HILL AND KELSEY Proc. N. A. S. 
ALKYL AMIDES OF ISOTHIOCY AN ACETIC ACID 
By Treat B. Johnson, Arthur J. H11.L and Erwin B. Kelsey 
Department of Chemistry, Yale University 
Communicated April 10, 1920 
Theoretically, anilides of chloracetic acid, of which chloracetanilide I 
is the simplest representative, might be expected to interact with potas- 
sium thiocyanate in two ways, namely, to form either a normal thiocya- 
nate or its structural isomer, an isothiocyanate, as is represented by 
formulas II and III, respectively. A careful study of this reaction, how- 
ever, has revealed the fact that it is productive only of the thiocyanate 
CICH2CONHC6H5 
I 
NCS.CH2CONHC6H5 SCN.CH2CONHC6H5 
II III 
form of these two isomers, or that combination in which sulphur is joined 
to carbon as represented in formula II. In every case, where the reaction 
has been represented as proceeding in the other manner, a careful examina- 
tion of the properties of the reaction-product has revealed an incorret 
interpretation of the change, and shown that the primary reaction-product 
possesses a different constitution than that of an isothiocyanate. In 
other words, we may conclude from the evidence thus far presented, that 
no anilide of isothiocyanacetic acid has yet been prepared.^ 
Wheeler and Johnson ^ submitted this reaction between potassium thio- 
cyanate and chloracetanilides to a very careful investigation and showed 
that the primary product of reaction is always a normal thiocyanate. 
They found, however, that these combinations are not always stable and 
in some cases it was extremely difficult to isolate them in a state of purity. 
This instability is explained by the fact that they easily undergo an unique 
rearrangement and are transformed into pseudothiohydantoins. In no 
case were normal thiohydantoins obtained by rearrangement. The isom- 
erization of thiocyanacetanilide may be represented as follows : 
CH2 S CH2 S CH2 S 
CO C : NCsHs 
\/ 
NH 
V 
The conclusions recorded in a recent publication by Beckurts and 
Frerichs^ have now forced us to turn our attention again to this field of 
CO— NHCeHs CO C : NH 
II 
N.CeHs 
IV 
