THE KANSAS UNIVERSITY 

 SCIENCE BULLETIN 



Vol. XIII. ] JULY, 1922. [No. 13. 



On Some Isothiourea Ethers.^ 



(Contribution from the Chemical Laboratory, University of Kansas.) 

 BY F. B. DAINS AND W. C. THOMPSON. 



ONE of the characteristic reactions of the substituted thioureas 

 is their ability to add directly alkyl halides, with the formation 

 of halogen halide salts of bases, in which the alkyl group is joined 

 to sulfur.- 



RNHCSNHR + R'X = RNHC(SR')NR,HX. 



From these salts, the free thiourea ethers can be obtained by the 

 action of alkalies. As part of an investigation now in progress, it 

 was deemed advisable to synthesize the n-propyl and n-butyl ethers 

 of certain thioureas and, owing to the departure of one of the 

 authors from this laboratory, to record these preliminary results at 

 this time. 



EXPERIMENTAL. 



r-PROPYL-a, )8-DlPHENYL THIOUREA. C6H.5NHC(SC3H7)NC6H5. 



(n-Propyl ester of phenylimino-phenyl thiocarbamic acid.) 



A mixture of thiocarbanilide (15 gms.) and normal propyl iodide 

 (10 gms.) was heated on the water bath for an hour. The light- 

 brown viscous liquid solidified on cooling. After crystallization 

 from alcohol the hydrogen iodide salt was obtained in the form of 

 colorless rhombic crystals, which melted at 103°. The salt was 

 slightly soluble in ether, cold water and cold alcohol, but readily 

 soluble in hot water, hot alcohol and acetone. The yield was 80 

 per cent. 



Calc. for CioHi8N,S,HI: N, 6.93. Found: 7.09, 6.79. 



The free base, which was insoluble in water, was obtained by 



1. The authors wish to express their thanks to the research committee of the University 

 for a grant which was of assistance in the prosecution of this work. 



2. Her. 14, 1490 (1881); 15, 1314 (1882); 21, 962, 1857 (1888). 



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