OF ARTS AND SCIENCES. 215 



mide. Nevertheless, all attempts to prove more definitely the for- 

 mation of such a product failed. When the amide was dissolved 

 in bromine and the solution treated with aqueous potassium hy- 

 droxide, a small yield of a substance insoluble in water was 

 obtained. This was filtered off, washed with water, and distilled 

 with steam. The best yield was obtained as follows. One part 

 of the amide was dissolved in 1.8 parts of bromine (about six 

 atoms of bromine to one molecule of amide) in a large beaker. 

 Over this solution was poured a considerable quantity of a cold 

 five per cent solution of sodium or potassium hydroxide. The 

 contents of the beaker were kept cold, and allowed to stand, the 

 alkaline reaction being maintained by the occasional addition of a 

 small portion of 20 per cent sodium hydroxide solution. The 

 insoluble product gradually rose to the surface, as the bromine 

 disappeared, and was skimmed off. It was washed with dilute 

 acid, and then distilled with steam. The yield was nearly 13 per 

 cent of the weight of amide taken. For further purification the 

 substance was crystallized from a very small quantity of alcohol, 

 solution being brought about at 90° to 100° under pressure. 

 The substance gave the following results on analysis : — 



I. 0.4259 grm. substance gave 0.3745 grm. C0 2 and 0.0160 grm. 

 H 2 0. 

 II. 0.2044 grm. substance gave 0.3082 grm. Ag.Br. 

 III. 0.2056 grm. substance gave 10.3 c. c. of moist nitrogen at 15°. 3 

 and 757.5 mm. pressure. 



in. 



5.84 



The analysis shows that the substance is not the expected amine, 

 but is /?S-dibromfurfuronitrile. This conclusion was confirmed 

 by the reactions of the substance, and by its preparation through 

 the dehydration of the amide, using phosphorus pentachloride as 

 the dehydrating agent. The amide was mixed with the calculated 

 quantity of phosphorus pentachloride, and the mixture heated in 

 a distilling flask to about 200°, until hydrochloric acid ceased to 

 be given off. The contents of the flask were then distilled with 

 steam. The yield of dibromfurfuronitrile was 56 per cent of the 



