118 THE UNIVERSITY SCIENCE BULLETIN. 



neutralizing an aqueous solution of the salt with sodium hydroxide. 

 The white needles, which separated from alcohol, melted at 61.5°. 

 Calc. for CieHigN.S: N, 10.39. Found: 10.10, 10.16. 



y-n-BUTYL-«, ^-DlPHENYL THIOUREA. C6H5NHC(SC4H9)NC6H5. 



The mixture of normal butyl iodide and diphenyl thiourea was 

 heated on the steam bath for an hour. The salt, which solidified on 

 cooling, could not be purified by crystallization. It was therefore 

 ground up and thoroughly washed with ether, in which it was in- 

 soluble. The yield of the hydroiodide, which melted at 122°, was 

 83 per cent. 



Calc. for Ci,H2oN2S,HI : N, 6.78. Found: 6.66, 6.68. 



An aqueous solution of the salt was treated with sodium carbon- 

 ate. The free base was obtained a heavy, colorless, noncrystalliz- 

 able oil, which was readily soluble in the ordinary organic solvents. 



Calc. for Ci,H2oN2S:N, 9.85. Found: 9.92,9.95. 



y-n-PROPYL-«, y8-Di-p-ToLYL Thioueea. C7H7NHC(SC.H7)NC7H7. 



Di-p-tolyl thiourea and normal propyl iodide reacted readily on 

 warming and the resulting hydrogen iodide salt was purified by 

 washing with cold alcohol. It then melted at 165°. The yield was 

 88 per cent. 



Calc. for C,,H22N2S,HI: N, 6.57. Found: 6.29, 6.51. 



The salt was freely soluble in water and the thio ether, precipi- 

 tated by the addition of alkali, crystallized from alcohol in fine, 

 white needles which had a melting point of 99°. 



Calc. for Ci8H,2N,S:N, 9.36. Found: 9.18, 9.35. 



r-n-BuTYL-«, /8-Di-p-ToLYL Thiourea. C7H7NHC(SC4H9)NC7H7. 



The hydrogen iodide salt, which was obtained in a 95 per cent 

 yield from the normal butyl iodide and the thiourea, melted at 145°. 



Calc. for Ci9H,,N2S,HI: N, 6.36. Found: 6.35, 6.35. 



The free base formed by neutralizing an alcoholic solution of the 

 salt was a thick, colorless liquid, insoluble in water but soluble in 

 organic solvents. 



Calc. for C,9H,,N2S:N, 8.97. Found: 9.12, 9.33. 



y-n-PROPYL-«, ^-Di-2, 4-Dimethyl-Phenyl Thiourea. 



(CH3)2C6H.3NHC(SC3H7)NC6H3(CH3)2. 



Di-m-xylyl thiourea and normal propyl iodide reacted easily on 

 warming, but the product, which was obtained in 87 per cent yield, 

 proved to be the free base and not its salt. This when purified from 

 alcohol melted at 113.5°. 



Calc. for C22H28N2S: N, 8.58. Found: 8.46, 8.46. 



