Synthesis of Amido-benzene. 301 



Synthesis of Diethyl Teimethyl Amido- 

 benzene. 



By R. F. Buttan, B.A., M.D., 

 Lecturer in Chemistry s Medical Faculty, McGill University. 



The general reaction on which this synthesis is based 

 was discovered by Prof, A. W. Hofman in 1872* This 

 eminent observer found that at high temperatures the 

 halogen salts of secondary, tertiary or even quaternary 

 bases of the aromatic series are converted into the salts of 

 their isomeric primary bases by a transfer of the fatty 

 radicles from the side chain to the nucleus. Thus the 

 hydriodide of monomethyl aniline at a high temperature 

 becomes converted into the corresponding salt of toluidine, 



C 6 H 5 , NH CH 3 =» C 6 H 4 CH 3 , NH 2 . 



This reaction has since found its way into chemical indus- 

 try, and is largely employed in the Berlin Aniline Factory 

 for the preparation of the higher homologues of aniline, 

 especially of Pseudo-cumidin, which is prepared from di- 

 methyl toluidine according to the following reaction : 



C 6 H, CH 3 N (CH 3 ) 2 ='C 6 H 2 (CH 3 ) 3 , NH 2 . 



It seemed a matter of much theoretical interest to test 

 the reaction still further, and by it to obtain, if possible, a 

 homologue of aniline in which all the hydrogen atoms of 

 the phenyl nucleus were replaced by radicles of the fatty 

 series. Taking as t a starting point this pseudo-cumidine, 

 in which three atoms of hydrogen out of the five are 

 already replaced by methyl, a modification of Hofmann's 

 method was employed to replace the other two hydrogen 

 atoms by ethyl groups, giving rise to the interesting prim- 

 ary base trimethyl diethyl amido-benzene : 



C 6 (CH 3 ) 3 (C 2 H 5 ) 2 NH 2 . 



How far the presence of methyl groups in the benzene ring 

 will retard or promote the introduction of further radicles 

 of another composition, has not yet been determined. This 

 synthesis is the first of a series of experiments designed to 



* Berichte der Deutschen Chemischen Gesellschaffc, v., 720. 



