Phenyliodide Chloride and Iodosobenzene Acetate. 555 
heated for several hours on the water-bath under a reflux. After 
filtering and distilling off the alcohol and ether, steam was con- 
ducted through the mixture to get rid of the phenyliodide. The 
residue was then extracted with ether, and on distilling off the 
ether a light brown oil remained behind. On re-distillation in 
vacuo, partial decomposition took place and a light brown oil 
distilled over. This oil did not contain any iodine. The yield 
was small. 
•095 grms. gave on combustion T855 C0 2 and '0460 H 2 0. 
0 = 53-25%, 
H = 5-36%. 
CH . CN . COOC 2 H 5 
requires C = 53 57 % and H = 5\35 %. 
CH . CN . COOC 2 H 5 
•088 grms. gave 9‘4c.c. of moist nitrogen at 758'6 mm. and 16 - 2° C. 
N = 12 43 %. 
CH . CN . COOC 2 H g 
j requires N = 125 °j . 
CH . CN . COOC 2 H 5 
The oil is therefore dicyansuccinic ester. 
Action of iodine on cyanacetic ester. 
Since in the former experiments the action of phenyliodide 
chloride on mono- and di-sodium malonic esters respectively is 
analogous to that of iodine on the same esters, an experiment was 
performed to see if the same parallel existed in the case of cyan- 
acetic ester. 
1123 grms. of iodine were dissolved in dry ether and allowed to 
flow gradually into a solution of sodium cyanacetic ester, which had 
been made by dissolving 2 - 03 grms. of sodium in absolute alcohol, 
adding 10 grms. of cyanacetic ester and then dry ether until 
turbidity appeared. 
During the addition of the iodine the mixture was well shaken, 
and heated for seven hours on the water-bath under a reflux. A 
large excess of dry ether was then added to precipitate all the 
sodium iodide formed. Distilled water was then added and the 
mixture well shaken to dissolve out all the sodium iodide. The 
ether layer was separated and shaken up with sodium thiosulphate 
until all the free iodine was dissolved out of the ether layer. 
The ether layer was then separated, filtered, and dried over 
CaCl. 2 . On distilling off the ether a light brown oil remained 
which was re-distilled in vacuo. A very good yield was obtained. 
The oil contained no iodine. 
