12 THE UNIVERSITY SCIENCE BULLETIN, 



The reaction mixture was dark colored and required long stirring 

 before the ammonium salt separated. It was then dissolved in 

 400 cc. of water and desulphurized. 



The isothiocyanate, which melted at 35°, was isolated by extract- 

 ing the sulphide precipitate with repeated portions of alcohol. The 

 product weighed 17.6 gms. (68.2 per cent). 



Beta-Naphthyl Isothiocyanate. 



The procedure was the same as with the alpha-naphthylamine, 

 and while the ammonium salt, which was readily formed, reacted 

 with the lead nitrate, no isothiocyanate could be isolated from the 

 residue using alcohol as a solvent. It is probable that some other 

 solvent would have proved more suitable. 



o-Anisyl Isothiocyanate. o-CHgOCgH^NCS. 



o-Anisidin 37 . 1 gms. 



Carbon bisulphide 27 . gms. 



Ammonium hydroxide 47 . gms. 



Alcohol 20 cc. 



Lead nitrate 100.0 gms. in 200 cc. of water. 



The ammonium salt separated quickly as a mass of coarse crys- 

 tals. The mixture was allowed to stand for one hour and then dis- 

 solved in 800 cc. of water and desulphurized. The mustard oil, 

 which distilled slowly with steam, weighed 35.2 gms. (70.7 per cent). 



P-Anisyl Isothiocyanate. p-CHgOC^H^NCS. 



p-Anisidine 10.0 gms. 



Carbon bisulphide 10.0 gms. 



Ammonium hydroxide 13.0 gms. 



Alcohol 15.0 cc. 



Lead nitrate 27.0 gms. in 500 cc. of water. 



The salt formed readily in large white crystals. After standing 

 two hours the mixture was dissolved in 500 cc. of water and treated 

 as usual. The mustard oil was easily volatile with steam and gave 

 a yield of 9.2 gms. (68.6 per cent). 



P-Phenetidyl Isothiocyanate. p-CoHjOCeH^NCS. 



In this case the weight of p-phenetidine was 41.3 gms.; otherwise 

 the amounts of reagents corresponded to those used in the prepara- 

 tion of the o-anisyl isothiocyanate. The mustard oil distilled 

 slowly with steam and gave a yield of 72.7 per cent. 



