22 



PROCEEDINGS OF THE AMERICAN ACADEMY. 



III. 



5.63 



a-Phenylamido-/3-bromcrotonolactone is almost insoluble in ether 

 carbonic disulphide, or ligroin, but dissolves somewhat more readily 

 in boiling benzol or chloroform. It is somewhat sparingly soluble 

 even in boiling alcohol, still less freely in boiling water, and as the 

 solutions cool is deposited in each case in long brilliant needles. In 

 hot glacial acetic acid the substance dissolves readily ; from chloroform 

 it crystallizes in thin transparent plates. When slowly heated it melts 

 with decomposition at about 165°, but if the capillary tube containing 

 the substance is plunged into the heated bath it melts promptly at 

 186-187° and immediately decomposes. In alkaline solutions it dis- 

 solves readily on warming, and if the solution be quickly cooled it 

 crystallizes out apparently unchanged, but on heating for a longer 

 time decomposition ensues, as the strong odor of pheuylisocyanide 

 shows. By the action of sodium amalgam bromine is removed and 

 a-phenylamidocrotonolactone, which we shall describe later, is formed. 

 We have been unable to replace the second atom of bromine by heat- 

 inff with an excess of aniline. 



Action of Hydriodic Acid. 



When o/3-dibromcrotonolactone is dissolved in ordinary distillable 

 hydriodic acid and the solution is boiled for a short time, or heated for 

 a longer time at 100°, one atom of bromine is replaced by iodine, and 

 as the solution cools the a-iod-/3-bromcrotonolactone separates in long 

 prisms. This same body is also formed by the action of phosphorous 

 iodide upon mucobromic acid or when hydriodic acid acts upon muco- 

 bromylbromide, and it may easily be made the chief product of the 

 latter reaction. For analysis it was recrystallized from alcohol. 



I. 0.2393 grm. substance gave 0.1453 grm. C0 2 and 0.0229 grm. H 2 0. 

 II. 0.1874 grm. substance gave 0.2747 grm. AgBr + 'AgI. 

 III. 0.2031 grm. substance gave 0.2978 grm. AgBr + Agl. 



C 

 H 

 Br + I 



Calculated for 

 C 4 II 2 BrI0 2 . 



16.61 



0.69 

 71.63 



I. 

 16.56 

 1.05 



Found. 

 II. 



71.76 



in. 



71.78 



