350 Mr. C. H. Browning and others. Relationships between 



[36-43.] 2.7 .Diaminoacricliiu Alhyl Chlorides. — In order to study the 

 relative antiseptic action of the quaternary alkyl derivatives of diamino- 

 acridine in addition to the methochloride (acriflavine), the ethyl, propyl, 

 m-butyl, isobutyl, isoamyl, phenyl, and benzyl chlorides were prepared, having 

 the following general formula : — 



CH 



N 



/\ 

 Alk CI 



The alkyl chlorides were obtained by the following method : A weighed 

 quantity of sodium was dissolved in the alcohol corresponding to the required 

 alkyl compound, and the theoretical amount of ^-toluene sulphonic chloride 

 added. After standing for a time, the product was shaken two or three times 

 with water. The washed product was dissolved in ether, dried over calcium 

 chloride, the ether distilled, and the residue heated in vacuo on the water- 

 bath. In this way the alkyl ^j-toluene sulphonic esters were obtained in the 

 form of pale yellow oils. 



CH 3 -C 6 H 4 .S0 2 Cl + RONa = CH 8 -C«H 4 -S0 3 E + NaCl. 



About 1 grm. of each ester was allowed to react with an equivalent weight 

 of diacetyldiaminoacridine in nitrobenzene solution at 150°-160° The 

 product in each case was hydrolysed with cone, hydrochloric acid, whereby 

 the alkyl chloride was obtained. 



The benzyl chloride compound, which was prepared in a similar way, was a 

 reddish brown crystalline substance, and on analysis 



0152 grm. gave 0132 grm. AgCl. CI = 216 per cent. Calculated for 

 C 20 H 17 N 3 C1 2 ; CI = 19-2 per cent. 



The phenyl chloride compound was obtained by dissolving phenol in the 

 calculated quantity of sodium hydroxide solution to form sodium phenate. 

 The equivalent amount of p-toluene sulphonic chloride was then added and 

 the mixture boiled for about half an hour, and cooled. The phenyl ^-toluene 

 sulphonic ester which separated was recrystallised from alcohol and melted 

 at 95°. It was transformed into the acridine phenochloride in the following 

 way : About 10 per cent, more than the theoretical amount of the ester 

 was added to the acetyl diaminoacridine dissolved in nitrobenzene and heated 

 for 5 minutes to 150°-160°. The product was cooled to 105°, when 5 c.c. of 

 cone, hydrochloric acid was added and the mixture maintained at 100° for 

 another 5 minutes and cooled to the ordinary temperature. The nitro- 



