482 Phelps, Weed, and Housum — Action of Dry Ammonia. 



under these conditions the production of the end product, 

 oxamide, is only a question of contact between the active 

 materials. To further test this conclusion the experiments of 

 Table II were tried. 











Table II. 





Oxamide 







Ethyl 

 oxalate 



Absolute 

 alcohol 



T . . Eeaction 



° time 





A 







Theory 



Found 



Error 



No. 



grin. 



cm 3 . 



cm 3 . 



min. 



grm. 



grm. 



grm. 



(1) 



8-231 



20 



— 



20 



4-965 



4-968 



0-003 + 



(2) 



6-554 



20 



— 



20 



3-953 



3-956 



0-003 + 



(3) 



6-033 



— 



10 



20 



3-639 



3-638 



o-ooi — 



Dry ethyl oxalate was weighed out in the dried apparatus 

 and treated with the dry ammonia in the cold, in presence of 

 absolute alcohol in experiments (1) and (2), and in presence of 

 a purified low-boiling ligroin in experiment (3). The time of 

 action of the ammonia was twenty minutes in each case before 

 the distillation which was made in (1) and (3) as previously 

 described, while in (2) all volatile material was removed with- 

 out raising the temperature. No evidence of unchanged 

 ethyl oxalate or of any ethyl oxamate appeared in any of these 

 experiments, although the flask was heated at 115° for the 

 removal of ethyl oxalate before weighing, and at 200° for the 

 removal of ethyl oxamate. The residue left in the flask was 

 taken, as in the experiments given in Table I, as the weight of 

 the oxamide produced. 



Hence it appears that dry ammonia in excess acts upon 

 anhydrous ethyl oxalate in the cold to form a mixture of ethyl 

 oxamate and oxamide as far as the ethyl oxalate is acted 

 upon ; and, if with the same proportion of reagents contact 

 between the dry ammonia and ethyl oxalate is facilitated 

 by a suitable medium such as ethyl alcohol or ligroin, the final 

 product produced in the same time appears to be oxamide 

 exclusively. 



