DAINS AND THOMPSON: ISOTHIOUREA ETHERS. 119 



THIOETHERS FROM UREAS CONTAINING TWO DIFFERENT 



GROUPS. 



r-METHYL-«-p-BROMOPHENYL-/8-PHENYL THIOUREA. 



aH5NHC(SCri.)NC6ll4Br or C«H.5NC(SCH3)NHC«H4Br. 



The iinsymmetrical nature of tlie mol did not prevent the addi- 

 tion of the alkyl iodide, since when methyl iodide and phenyl-p-bro- 

 mophenyl thiourea were heated under the usual conditions a yield 

 of 69 per cent of the hydrogen iodide salt was obtained. It melted 

 at 152°. 



Calc. for Ci,Hi3N,SBr,HI : N, 6.24. Found: 6.04, 6.27. 



The thioether was preciptated when an alcoholic solution of the 

 salt was made alkaline with sodium carbonate and then diluted with 

 water. When purified, the white needles melted at 79°. 



Calc. for Ci,Hi3N2SBr; N, 8.72. Found: 8.54,8.77. 



r-n-PROPYL-'>t-p-BROMOPHENYL-/3-PHENYL THIOUREA. 



CeH.NHC (SC3H7) NC6H4Br. 



Normal propyl iodide and the thiourea united to form a salt, 

 which, however, failed to crystallize, but remained as a heavy, 

 red oil. 



Calc. for Ci,Hi-N,SBr,HI: N, 5.88. Found: 5.46. 



The thioether, which was isolated in a 70 per cent yield, melted at 

 84°, after purification from alcohol. 



Calc. for CisHi-N.SBr; N, 8.02. Found: 8.09, 8.07. 



y-n-BuTYL-'Z-p-BROMOPHENYL-yS-PHENYL THIOUREA. 



C6HoNHC(SC4H9) NC6H4Br. 



The hydrogen iodide salt from the thiourea, and the normal butyl 

 iodide separated in this case also as a thick noncrystallizable oil. 



Calc. for Ci,H,9N.SBr,HI; N, 5.70. Found: 5.37, 5.62. 



The free base obtained in the usual manner was a viscid oil, sol- 

 uble in alcohol and ether. 



Calc. for Ci-H.^N^SBr; N, 7.71. Found: 7.72, 7.52. 



r-n-BuTYL-MoNOPHENYL THIOUREA. C6H5NHC(SC4H9)NH. 



When monophenjd thiourea and normal butyl iodide were warmed 

 on the water bath, a gummy mass was obtained. This was dissolved 

 in hot alcohol and neutralized with sodium carbonate. On dilution 

 with water the thiourea was precipitated as a heavy oil, which failed 

 to crystallize. 



Calc. for C11H16N2S; N, 12.72. Found: 13.03, 13.05. 



