( 45 ) 



No further attention has been paid of late to this production of 

 oxalic acid, whicli might most likely be obtained from substances 

 other than oxalyklerivatives, for instance, mesoxalic acid derivatives. 



As the above reaction appears to take place with all the hydro- 

 chlorides of aminoesters as j'et examined, it may be expected that 

 similar oxalylcompounds will be obtained from the polypeptides in 

 general, which might be looked on as building stones of the proteid 

 molecule. 



But little attention is also paid to the production of carbon 

 dioxide in the resolution of the albumenoids and yet — like the 

 oxalylcompounds of the polypeptides — their carbonyl compounds 

 might also be building stones of the proteid molecule. Provisional 

 experiments with simple amides showed that by the action ofoxalyl 

 chloride no oxalyl-, but carbonylderivatives were obtained because 

 oxalylchloride behaves in some cases as a source of carbonylchloride. 



With acetamide (boiling in benzene) I obtained in this way 

 diacetylurea and with chloroacetamide carbonyldi(chloroacetamide) 



/NH CO CH, CI 



CO crystallising in delicate vvhite needles m.p. 171° C. 



^NH CO CH, CI 

 Whith benzamide dibenzoylurea was formed but with benzanilide, 



CO NC« H, COC3H3 

 on the otherhand, oxalyldi(benzanilide) | was obtained 



CO NCe H, COCeH^ 

 in beautiful needles melting at 210° C. 



C0N(C,HJC0CH. 

 Acetethylamide gave oxalyldi(acetethylamide) | 



C0N(C,H,)C0CH3 

 in beautiful crystals melting at 130° C. 



Whereas ethylurethane yielded carbonyldi(ethylurethane) I obtained 

 with methylethylurethane oxalyldi(methylethylurethane) 



CO NCH3 COOC.H, 



I 



CO NCH3 COOC.H, 



in clear white needles m. p. 67° C. 



It thus appears that with mono-alkylamides the reaction leads to 

 oxalylderivatives but with simple amides to carbonylderivatives. 



With urea, which may also be classed among the amides were 



obtained (in ether at the ordinary temperature) parabanic acid and 



CONHCONH, ^.^ 

 presLimablv, the true oxalyldiureid • different from the 



CO iN XI CU jN H J 



