116 PROCEEDINGS OP THE AMERICAN ACADEMY 



C1C,H 4 N=C ' 



NH 2 



because on treatment with caustic potash it is converted into 

 chloraniline. 



The product described as isotriphenylguanidine hydrochloride 

 (mpt. 207°) was either the salt of a chlorinated triphenylguani- 

 dine, or perhaps still a mixture. 



Sell and Zierold state that on passing chlorine gas into phenyl- 

 mustard oil no substitution takes place; it follows that probably, 

 on fractionating the products of the reaction, C 6 H 5 N = CC1 2 + SC1 2 , 

 chlorine is set free,* and then substitution takes place. That this 

 is so is proved by the following experiment, which leads to pure 

 isocyanphenyl chloride. 100 grams of phenyl mustard oil were 

 treated according to the directions given by Sell and Zierold with 

 chlorine, and, as soon as no more absorption of the gas is noticed, 

 the chloroform solution is poured slowly, with thorough shaking, 

 into much water, in order to decompose the SC1 2 formed. The 

 chloroform solution, after treating with sodic hydrate, is dried with 

 calcic chloride, and on fractional distillation a colorless oil ob- 

 tained boiling at 204°-205° (80 grains), which is identical in 

 every particular with the product obtained from phenylisocyanide 

 and chlorine. On treatment with aniline it is converted into tri- 

 phenylguanidine hydrochloride (mpt. 241°). The free base ob- 

 tained therefrom melts at 143°, and a nitrogen determination gave 

 the following result : — 



0.2142 gram substance, dried at 105°, gave 27.5 c.c. moist nitrogen 

 at 19°, and 748 mm. 



Theory for C 19 H 17 N 3 . Found. 



N 14.63 14.52 



An analysis of the isocyanphenylchloride obtained from phenyl- 

 mustard oil and chlorine gave the following results : — 



0.1542 gram substance gave 0.2725 gram C0 2 and 0.0431 gram 



H 2 0. 

 0.3003 gram substance gave 21.1 c.c. moist nitrogen at 20° and 



756 mm. 

 0.1052 gram substance gave 1754 gram AgCl on ignition with 



CaO. 



* SC1 2 is decomposed by distillation, as is well known, into S 2 C1 2 and Cl 2 . 



