280 P. T. Austen— Niiro-derivatives of Diphenylamine. 



sation of the action, most of the phosphorous oxychloride was 

 distilled off. The heavy red liquid, remaining in the retort, 

 was poured into a large excess of cold water and violently 

 stirred. After the phosphorous oxychloride had been entirely 

 decomposed by the water, and the mass had solidified, the 

 impure substance was well washed with water, powdered, and 

 extracted with ether by means of a filter pump. A dark-red 

 resin was by this means removed. The bright yellow powder, 

 left on the filter, was dissolved in boiling absolute alcohol and 

 purified by animal charcoal. 



In this manner beautiful bright yellow crystals of trinitro- 

 chlorbenzol were obtained. By drying they became darker. 

 The yield is from 30-40 per cent. 



I obtained better results, however, by simply heating the 

 substances in a high beaker glass, for I found that a consider- 

 able amount of the chlorpicryl was destroyed during the distil- 

 lation of the phosphorous oxychloride. I found, also, that 

 the yield was far better, when 'instead of 100 grams of picric 

 acid and 200 grams of phosphorous pentachloride, 50 grams of 

 picric acid and 100 grams of phosphorous pentachloride were 

 taken. By this method the conversion of the picric acid into 

 ;.i. the decomposition of the phosphorous oxychloride, 

 the extraction with ether, and the crystallization from alcohol, 

 all together do not take more than an hour. 



The trinitrochlorbenzol fused at 82-5°-83°. By dissolving 

 it in glacial acetic acid, diluting the solution with water, and 

 allowing it to stand, superb feathers, frequently over two inches 

 in length, were obtained. 



Alphatri 'aniline.* 



Preparation.— 25 grams of metanitraniline (112°) and 27 

 grains of chlorpicryl were dissolved in boiling absolute alcohol. 

 On boiling the solution for a few minutes, the separation of a 

 he v; ve low - , lline sai d be- m This sand was not redis- 

 . Mite .n of more alcohol. The solution was allowed 

 to cool, the precipitate separated by filtration, purified by crys- 

 tallization from glacial acetic acid, dried at 100°, and analyzed. 



Analysis. — A combustionf gave — 

 02744 grms. of substance burned with lead chromate gave 0*414 



grms. of CO 3 and 0-582 grms. of H 2 0. 

 0-2752 grms. of substance gave V=48"8 c.c. rB = 7o4-8 mm. ; **= 



21 -5° i. ° L 



