238 Messrs. Dakin, Cohen, Daufresne, and Ken von. 



neutral solution X-dichloropentamethylenetetramine is obtained, while in 

 acetic acid solution trichlorohexahydrotriazine is formed.* 



Practical. 



Preparation of Substances. — The action of sodium hypochlorite on the 

 sulphonamides was first examined by Eaper, Thompson and Cohen.f Later, 

 Chattaway, by a similar reaction, prepared a series of sulphochloramides, 

 details of which can be found without difficulty in the ' Trans. Chem. Soe.' 

 Eeferenee will be made here simply to substances which had not been 

 hitherto obtained by others, or for the preparation of which improved 

 methods have been adopted. 



A number of new sulphochloramides were prepared from the corresponding 

 hydrocarbons by successive formation of the sulphonic acid, sulphonic 

 chloride, sulphonamide, and sulphodichloramine. The latter substances were 

 converted into the sodium sulphochloramides by the action of sodium hydroxide 

 according to Chattaway's method.^ 



E.S0 2 .XH 2 + 2HC10 = E.S0 2 XC] 2 + 2H 2 0. 

 E.S0 2 NC1 2 + 2NaOH = E.S0 2 Na : NCI + NaCIO + H 2 0. 



The sodium sulphochloramides of the following hydrocarbons had not been 

 previously obtained : o-, m- and js-xylene, ethylbenzene, ehlorobenzene,§ 

 diehlorobenzene, bromobenzene, iodobenzene, mesitylene, pseudocumene, 

 dibenzyl. They are all soluble crystalline salts, sparingly soluble in caustic 

 soda solution, and give the general reactions for chloramines. The sodium 

 salts of the sulphochloramides of diphenyl and diphenylmethane, and 

 2.6 naphthalene sodium sulphochloramide were obtained in solution by 

 decomposing the corresponding dichloramines with hot sodium hydroxide and 

 then neutralising the solution. 



We have found that a number of sodium sulphochloramides, including 

 those of benzene and toluene, may be conveniently and economically made 

 by a process which avoids the intermediate preparation of the sulpho- 

 dichloramine. This method simply consists in dissolving the powdered 

 sulphonamide (1 mol.) in a cold solution of sodium hypochlorite (1.2 mols.), 

 warming and filtering if necessary, and then adding one and a half volumes 

 of saturated brine. The sodium salt of the sulphochloramide crystallises out 



* ' Bull. Soc. Chim.' (iv), vol. 9, p. 1025 (1911). 

 t ' Trans. Chem. Soc.,' vol. 85, p. 371 (1904). 

 % 'Trans. Chem. Soc.,' vol. 87, p. 145 (1905). 



§ Since this work was completed, Chattaway has described the three mono-halogen 

 benzene sodium sulphochloramides. ' Trans. Chem. Soc' vol. 107, p. 1814 (1915). 



