REARRANGEMENT OF X-BENZYLBENZALDOXTME. o 



generated in the reaction, the author and Kainoshö^ having ah-eady 

 observed the actual production of phenylbenzamide, CcHg-CO- 

 NH . CJir,, fi'om phenylbenzimido-chloride CgH,^ • C CI : N • CgHj, 

 by the action of acetic acid. Thus, the rearrangement when acetyl 

 chloride is used may be represented by the following scheme: 



CflH-— CH\ +CII3COC1 

 I O — ^ 



( C,H,— CHCl ^-cii3C0()n C,^H,— CCI 



C.-H.CH.NO.COCHJ CcH^CH^N 



CgH-— CI CH, CO C,H-— CO 



li + I = I + CH3COC1. 



C„HgCH,N H C,H,,CH,NH 



The acetyl chloride thus formed in the last stage of the reaction 

 will act upon the fresh portion of the N-ether, forming the addi- 

 tion product as before, immediately followed by the formation of 

 benzylbenzimido-chloride with the separation of acetic acid, which 

 will bring about the decomposition of the imido-chloride into 

 benzylbenzamide, so that the same process continues until the 

 iST-ether is exhausted. A small quantity of the acid chloride must, 

 therefore, be theoretically possible to convert an infinite quantity 

 of N-benzylbenzaldoxime to benzylbenzamide, the acid chloride 

 apparently remaining unchanged or acting as a catalyser. 



The rearrangement of N-benzylbenzaldoxime in presence of 

 an acid anhydride, such as acetic or benzoic anhydride, however, 

 appears to proceed in a somewhat different way, because Beck- 

 mann" claims to have obtained acetyl and benzoyl benzylbenz- 

 amides as the chief products of the rearrangement. 



Experimental : — By gradually adding an equivalent quanti- 



1. Memoii-s, College of Science :iiid Engineering, Kyoto, Vol. I, 259. 



2. Ber. deut. chem. Gesell., 26, 2274. 



