376 PROCEEDINGS OF THE AMERICAN ACADEMY 



dissolved in glacial acetic acid, — a method which gives the trichlor- 

 aniline more quickly than any of the others, but which we discarded 

 on account of the very small yield obtained. 2d. According to Beil- 

 stein and Kurbatow,* by the formation of chloracetanilid from chlorine 

 and acetanilid, and converting this, after the removal of the acetyl, 

 into trichloraniline by treatment with chlorine in a glacial acetic acid 

 solution. We may be allowed to remark, in regard to this method, 

 that we were unable to make acetanilid in glacial acetic acid solution 

 take up moie than one atom of chlorine, an excess of chlorine passing 

 through the solution unaltered after monochloracetanilid had been 

 formed, whereas Beilstein and Kurbatow obtained the dichloracetanilid 

 in this way ; we have not thought the point of sufficient importance, 

 liowever, to devote to it the time necessary to determine the cause of 

 this difference. This method gives good results, but does not lead to 

 them so quickly and easily as the third, which consists in making di- 

 chloracetanilid according to Witt, f that is, acting on acetanilid in a 

 warm acetic acid solution with a solution of bleaching-powder. The 

 dichloracetanilid was then converted into the trichloraniline, as in the 

 second method. 



The method, therefore, which we finally adopted, and should recom- 

 mend as the best, is the following : 5 parts of acetanilid are dissolved 

 in 20 parts of glacial acetic acid and 100 of water, and heated to 

 boiling; then, after removing the lamp, a 10 per cent solution of 

 bleaching-powder is added, until a viscous precipitate is formed, the 

 temperature being kept above 70°. The precipitate is then treated 

 with amnionic hydrate, and crystallized from alcohol. The yield of 

 dichloracetanilid is nearly quantitative. The dicliloracetanilid is next 

 converted into dichloraniline by heating it on the water-bath with 

 strong sulphuric acid, the dichloraniline dissolved in glacial acetic 

 acid, and chlorine passed through the solution until two parts of the 

 dichloraniline have gained one part of chlorine ; the product is then 

 rendered alkaline with a large excess of sodic hydrate, and distilled 

 with steam ; the solid which distils over, after crystallization from 

 dilute alcohol, is pure trichloraniline, but the yield is far from satis- 

 factory, a large quantity of tarry impurity being formed during the 

 treatment of the free base with chlorine. The trichloraniline is con- 



* Ann. Chem., clxxxii. 95. 



t Ber. d. oli. G., 1875, p. 1226. Bender, Ber. d. di. G., 1886, p. 2272, has 

 obtained CgHsNClCOCMs by the action of bleaching powder on a cold acetic 

 acid solution of acetanihd. 



