CHEMICAL AND PHYSICAL PAPERS. 71 



THE ACTION OF ETHYL CHLORSULFONATE UPON 

 ANILINE. 



By F. W. Bdshong, Kansas City University, Kansas City, Kan. 

 Read before the Academy, at Topeka, December 31, 1904. 



A STUDY of the action of sulfuryl chloride and of ethyl chlor- 

 sulfonate upon aniline, dimethylaniline and acetanilide was 

 first undertaken by Wenghoffer/ who drew the following conclusions 

 from the results of his experiments : 



I. By the action of sulfuryl chloride upon aniline and upon ani- 

 lides chlorine substitution products are obtained. 



By the action of ethyl chlorsulfonate upon these bodies, products 

 are formed which contain the — SOiOH group, bound directly to the 

 benzene nucleus. With aniline, for example, he obtained sulfanilic 

 acid. 



J. Wagner'- prepared a body from pyridine and chlorsulfonic 

 acid which had the composition Cr.H.^NSOs, and which, with water or 

 alcohol, decomposed, forming pyridine sulfate and sulfuric acid, 

 or ethylsulf uric acid, respectively ; and found that on dissolving it 

 in aniline and adding ether, crystals of the aniline salt of phenyl- 

 sulfarainic acid separate. He pointed out that Wenghoffer prob- 

 ably overlooked this salt, owing to the fact that he treated his crude 

 reaction product with water. 



W. Traube^ isolated salts of aromatic sulfaminic acids, which he 

 obtained by treating aromatic amines with chlorsulfonic acid, and 

 Bamberger"* has studied the transformation of phenylsulfaminic 

 acid into sulfanilic acid. 



It seemed desirable, therefore, to again take up the study of the 

 action of ethyl chlorsulfonate upon aniline. 



Ethyl chlorsulfonate (1 mol.) was dropped into an ice-cold 

 ligroin solution of aniline (3 mols.) Each drop instantly produced a 

 white crystalline precipitate. The crystals were thrown upon a filter 

 and washed, first with ligroin, afterwards with absolute ether. The 

 ligroin solution was found to contain ethyl aniline, which was identi- 

 fied by converting it into ethylphenylnitrosamine. No trace of an 

 ester could be found in either the ligroin or ethereal solution. A por- 

 tion of the crystalline precipitate, heated to 150", gave off vapors re- 



1. J. prakt. Chem,, (2), 16, 448 (1877), 



2. Ber. d. chem. Ges.. 19, 1157 (1886). 



3. Ber. d. chem. Ges., 23, 1653 (1890). 



4. Ber. d. chem. Ges., 30, 2275 (1897). 



