377 



very little had crystallized out and a fiirtlier tritling quantity was 



recovered by distilling off the benzene. The distillate had a strong 



odour of wobutyrk nitrile and evolved much ammonia when boiled 



with potassiumhydroxide ; it did not contain any previously. Boiling 



with strong hydrochloric acid first and then with potassiumhydroxide 



also yielded ammonia which likewise points to the presence of the 



said nitrile. The solid product was but little soluble in cold water 



or ether ; after being extracted with both it was recrystallized a few 



times from alcohol and then melted at 160°. When heated with 



aqueous potassium hydroxide it gave oxalic acid. On analysis were 



obtained figures corresponding with those required by oxalyllmiso- 



CO-NH-CO-C,H. 



I 

 butyrylamideCO-^R-CO-^ja^. Hence there was obtained, not as was 



expected from the results obtained by Bornwater with other amides, 



a carbonyl, but an oxalyl derivative, whilst the greater part of the 



amide had been converted into nitrile. Hence, the oxalylchloride 



had acted to a large extent as other acid chlorides and anhydrides 



do sometimes, namely caused formation of water. Perhaps this 



happens also with other amides and to this might be attributed the 



frequent bad yield. Why no carbonylderivative but an oxalyl 



derivative has formed here remains for the moment obscure. 



As isobutyrylmetkylamide CaH^-CO-NH-CHj was not known, I have 

 prepared this also and I found again confirmed the regularity, to 

 which I have pointed previously ^), that inethylamides have a lower 

 melting point tlian the amides. It was prepared from /^'obutyryl 

 chloride and methjlamine in ethereal solution at a low temperature 

 and distilled under a diminished pressure. At 17 in.m. it passed 

 over constantly at 110° as a colourless liquid. On cooling it ciystal- 

 lized and again melted at fully 20°. The analysis showed its purity. 

 In supermelted condition at 16° the sp. gr. was 0,9089. 



The efhanesulphonamide, obtained by James from the chloride 

 with ammonia in ether, was prepared by me in the same manner; only 

 the melting point 1 found a little higher (60°) and not 58°. From 

 benzene in which it is little soluble it crystallizes in long delicate 

 needles, from ether, in which it is more soluble, in thick prisms, 

 likewise from acetic ether and acetone in which it is freely soluble. 

 Boiled for seven hours with oxalylchloride in benzene it deposited 

 a solid substance, whilst in the benzene was dissolved but little of 

 a brown syrupy mass, which was left on distillation. It may be 

 recrystallized both from water and alcohol, although it is decom- 



i) Rec. d. tr. ch. d. P. B. T. XVI. p. 12S. 



