OF ARTS AND SCIENCES. 245 



XI. 



CONTRIBUTIONS FROM THE CHEMICAL LABORATORY OF 



HARVARD COLLEGE 



ON THE DIRECT CONVERSION OF AROMATIC SUL- 

 PHONATES INTO THE CORRESPONDING AMIDO 

 COMPOUNDS. 



By C. Loring Jackson and John F. Wing. 



The action of sodium or potassium amide on organic substances has 

 been studied but little ; in fact, when we took up the subject, there 

 were no papers more recent than those of Beilstein and Geuther * on 

 fiodium amide in 1858, and of Baumert and Landoltf on potassium 

 amide in 1859. The reason for this neglect may be found probably 

 in the curious observation made in both of these pajjers, that the alka- 

 line amides are not acted on in the way which we should expect by 

 most haloid organic compounds, neither ethylchloride, or iodide, nor 

 chlorbenzol, nor acetylchloride giving the corresponding amido com- 

 pounds ; t in fact, benzoylchloride is the only haloid organic compound 

 tried which acted as would be expected, giving benzamide and di- 

 benzamide. Accordingly, in taking up the subject, we have turned our 

 attention to the effect of sodium amide on sulphonates, in the hope of 

 obtaining an action similar to the well-known replacements of the 

 sulplio-group by hydroxyl, cyanogen, or carboxyl, when fused with 

 potassic hydrate, cyanide, or formiate respectively. This expectation 



* Ann. Cliem., cviii. 88. 



t Ibid., cxi. 1. 



t These results so far as the ethyl compounds are concerned have been 

 confirmed recently by J. Walter, who, in a paper ( Journ. pr. Chem., xxxiv. 132) 

 drawn out by the preliminary notice of our work, states that at low tempera- 

 tures no ethylamine is formed from ethylbromide ; but by heating the sodium 

 amide until it begins to melt, and passing over it a stream of hydrogen impreg- 

 nated with ethylbromide, ethylamine was formed, recognized by the carbylamine 

 reaction. Under similar conditions brombenzol gave small quantities of aniline. 

 He however does not consider it proved, that tlie amine was formed from the 

 sodium amide, rather than from the ammonia set free during the reaction. 



