PURDIE'S REACTION 213 



Aceto-p-toluidide differs from its o-isomer in being con- 

 verted by silver oxide and methyl iodide into N-methyl- 

 aceto-p-toluidide only. By similar methods, N-a- and 

 N-/?-napthylacetiminoethyl ethers were prepared from 

 aceto-a- and aceto-/8-napthalides, and N-phenylbenzimino- 

 ethyl ether C 6 H 5 . N : C(OC 2 H 6 ) . C 6 H 5 from benzanilide. The 

 latter substance gives rise to the corresponding methyl ether 

 mixed with a little benzoylmethylaniline when subjected to 

 the action of silver oxide and methyl iodide (13) and the 

 benz-o- and benz-p-toluidides behave similarly. 



Under parallel conditions derivatives of oxalic acid yielded 

 results in agreement with those already mentioned. Thus 

 oxanilide was converted into di-N-phenylimino-oxalic diethyl 

 ether(C 6 H 5 . N: COEt) 2 and ethyl oxanilate into semi-N-phenyl- 

 imino-oxalic diethyl ether. On the other hand, methyl 

 oxanilate in benzene solution, when alkylated by means of 

 silver oxide and methyl iodide, gave semi-N-phenylimino- 

 oxalic dimethyl ether C0 2 Me . C : (NPh) . OMe along with some 

 isomeric methyl phenylmethyloxamate COgMe . CO . NMePh 

 (24). The effect of ethylating methyl oxanilate in the usual 

 manner was somewhat curious. A product intermediate in com- 

 position betweenC0 2 Me.C:(NPh)OEt and C0 2 Et.C:(NPh)OEt 

 resulted, and interchange of alkyls in the carboxylic ester 

 group must therefore have occurred during the ethylation of 

 the CO . NH residue. 



A preliminary attempt to prepare a toluimino-ether from 

 o-toluamide resulted only in the conversion of the latter into 

 o-toluonitrile. This attempted alkylation was carried out in 

 boiling alcoholic solution, and it was afterwards found that 

 different amides (21), under the same conditions, give rise to 

 nitriles together with some imino-ether. Thus whilst o-tolu- 

 amide gives a 13'6 per cent, yield of the imino-ether, p-tolu- 

 amide gives a 70 per cent, yield. This result is explained by 

 supposing that the o-compound loses alcohol more readily than 

 its p-isomeride : C 7 H 7 . C : NH . OEt > C 7 H 7 . CN+EtOH. 



