IX, A, 2 Py^att and Brill: Phthalide Compounds 117 



porcelain boat. The red oxime rapidly turned purple, and gained 

 in weight corresponding to the addition of one molecule of NH3. 



Formation of ammonium salt of thiophthaloxime. 



Sample. Gain. Gain. 



Gram. Gram. Per cent. 



0.3195 0.0285 8.92 



Calculated for CsH.O.NS-NH^ 8.68 



The salt did not lose ammonia when exposed to a current 

 of carefully dried air, but rapidly became colorless in the presence 

 of moisture. 



The silver salt forms at once as a purple precipitate when 

 a solution of silver nitrate is added to the oxime dissolved. in 

 absolute alcohol or to an aqueous solution of the ammonium salt. 

 In both cases, the salt undergoes decomposition almost im- 

 mediately with the formation of silver sulphide. No analysis, 

 therefore, of the silver salt was attempted. 



THIOPHTHALOXIME ACETATE 



c=s 



C6H4<^)>0 



C=N0C0CH3 



Thiophthaloxime acetate was made by allowing the oxime 

 to stand overnight at room temperature in the presence of 

 an excess of acetic anhydride. The oxime slowly goes into 

 solution under these conditions, and the acetate may then be 

 precipitated in nearly quantitative yield by the addition of 

 water. It is very soluble in acetic acid and in ethyl alcohol, from 

 which it crystallizes in orange plates melting without decomposi- 

 tion at 104° (corrected). 



Analyses of thiophthaloxim,e acetate. 



Substance. '^^"aUdd" Nitrogen. 



Gram. cc. Per cent. 



0.2078 9.41 6.35 



0.2109 9.52 6.32 



Calculated for CoH^OaNS 6.34 



Substance. ^""p'h^te."'' Sulphur. 



Gram. Gram. Per cent. 



0.2370 0.2340 13.57 



Calculated for C,oH,0,NS 14.52 



Thiophthaloxime acetate in alcohol gave an absorption spec- 

 trum differing from that of thiophthaloxime only in the extent 



