Vol. 6, 1920 CHEMISTRY: JOHNSON, HILL AND KELSEY 
291 
research. These investigators have included in their recent work several 
new anilides of chloracetic acid, and in the case of three of them they 
interpret the reaction with potassium thiocyanate as leading to the forma- 
tion of isothiocyanates. The anilides which interact with potassium thio- 
cyanate in this unique manner are the m-toluide, ^-chloranilide and p- 
anisidide of chloracetic acid. 
In the light of these interesting results, it has become necessary for us 
to take up again this question of constitution from an entirely new view- 
point, and apply the synthetical method of investigation. The question 
of tautomeric behavior of potassium thiocyanate must be excluded from 
further consideration, and a fundamental method of synthesis be developed 
whereby only true isothiocyanate combinations corresponding to formula 
III can be formed. At present such a method of synthesis is not known. 
These isothiocyanates if formed would not revert by rearrangement to 
normal thiocyanates, and should exhibit a chemical behavior quite as 
characteristic as that of the isomeric thiocyanates. Theoretically combina- 
tions corresponding to formula III should easily undergo isomerization 
with formation of normal thiohydantoins. In other words, if the isothio- 
cyanate III is a product of reaction when potassium thiocyanate inter- 
acts with chloracetanilide as Frerich and Beckurts assume, it should act 
in an entirely different manner than the thiocyanate II and isomerize to 
the same hydantoin VI, as is obtained by interaction of phenylisothio- 
cyanate with glycine"^ or its ethyl ester. These changes are represented 
as follows: 
CICH2CONHC6H5 — ^ SCN.CH2CONHC6H5 
III 
QHsN CO 
--^ CS ^ 
I 
NH CH2 
VI 
CeHsNCS + NH2CH2COOH— >C6H5NHCSNHCH23COOH 
We are now in position to report a practical method of synthesis which 
enables us to obtain anilides of isothiocyanacetic acid. Starting with 
chloracetanilide for illustration the complete operation may be outlined 
as follows : Chloracetanilide is first converted into the anilide of glycocoU 
(glycine) VII, and this then combined with carbonbisulphide when the 
corresponding dithiocarbamate VIII is obtained in excellent yield. This 
salt VIII is a crystalline substance melting at 145 ° and its formation from 
chloracetanilide is expressed as follows: 
CICH2CONHC6H5 + 2NH3 = NH4CI + NH2CH2CONHC6H5 
VII 
