142 PROCEEDINGS OF THE AMERICAN ACADEMY 



then heated in a sealed tube for four hours at 100°. The hydro- 

 gen sulphide had completely disappeared, and, after distilling off 

 the alcohol, the residue was taken up with ether and shaken with 

 sodic hydrate. On acidifying the alkaline solution, thioform- 

 o-toluide separates out in yellow, bulky flakes; recrystallized three 

 times from ligroine (bpt. 70°-80°), using animal charcoal, it is 

 obtained in perfectly colorless needles, melting at 106°-101°. Se- 

 nier* describes thioform-o-toluide as a yellow substance, melting 

 at 94° -96° (crystallized from alcohol). 



0.1986 gram substance, dried at 70°-80°, gave 0.2928 gram 

 BaS0 4 (Carius). 



Theory for C 8 H 9 NS. Found. 



S 21.19 20.29 



Isocyan-o-tolylchlorlde or o- Tolylimidocarbonylchloride, 

 CH 3 -C 6 H 4 N=C=C1 2 . 



This substance is formed quantitatively on passing dry chlorine 

 into a chloroform solution of o-tolylisocyanide, as above in the case 

 of isocyanphenylchloride. As soon as the presence of unabsorbed 

 chlorine can be detected, the reaction is ended, and the solution 

 immediately washed with dilute sodic hydrate, and dried with 

 calcic chloride. On fractionating, a colorless sharp-smelling oil is 

 obtained, which "boils at 214°-215° (uncorr.). 



0.1384 gram substance gave 0.2593 gram C0 2 and 0.0520 gram 



H 2 0. 

 0.2230 gram substance gave 15 c.c. moist nitrogen at 23° and 



756 mm. 

 0.2103 gram substance gave 0.3201 gram AgCl (Carius). 



o-Toluidine converts the isocyan-o-tolylchloride quantitatively 

 into o-tritolylguanidine hydrochloride. In order to isolate the 

 free hase, the solution is made slightly alkaline, and the excess of 

 toluidine got rid of by distilling with steam. The residue, recrys- 

 tallized twice from alcohol, gave flat needles of o-tritolylguanidine, 



* Ber. d. chem. Ges , XVIII 2293. 



