118 



Chlorine was evolved and a white solid separated which was very soluble 

 in water. The aqueous solution after standing some time gave ofiE a 

 distinct odor of benzoic ether (CsHoCOOOHs). Caustic soda separated 

 from the solid an oil which had the characteristic odor of benzimido ether 

 ( CgHsCH^'Jf ) . -^ quantity of the salt was heated in a bath to 118°. 

 A gas (CH3CI) was evolved Avhich burned with a green flame, and iu the 

 tube there remained a crystalline substance which proved to be benza- 

 mide. Some of the methylated chloramide was suspended in water and 

 reduced with hydrogen sulphide. When the oil had become dissolved 

 the solution was poured from the fi'ee sulphur and distilled with a con- 

 centrated solution of caustic soda, the distillate being collected in hydro- 

 chloric acid. This distillate was evaporated to dryness, and the residue 

 extracted with absolute alcohol. Very little dissolved in tlie alcohol and 

 no trace of methyl amine could be detected, nor of aniline by using 

 either the delicate Jacquemine test or the isoeyanide reactiou. The prop- 

 erties of this substance therefore and its reactions correspond in every 

 detail with what would be expected from the constitution, 



p TT p — OCH3 



^6 "5'^ = NCI. 



Besides, benzchloramide is a fairly strong acid, as its alcoholic solution 

 can lie titrated against standard caustic alkalis, using either phenol- 

 phthalein or litmus as indicator. This acidity is not due to hydrolysis, thus 

 foi'ming free hydrochloric acid, since it gives with silver nitrate, even 

 on standing, only a trace of silver chloride. A solution of the substance 

 therefore contains hydrogen ions, a thing not to be expected on the suppo- 

 sition of an amide hydrogen. We may conclude therefore that benzchlor- 

 amide contains an hydroxjd group. 



Attempts were made to extend the investigation to other amides, viz., 

 m— nitrobeuzamide and anisic acid amide. The chloramide of the former 

 however was found to be so unstable even at 0° that work on it was 

 discontinued for the time. Anisic acid chloramide is also unstable, but 

 at —5° enough of it was obtained to try the action of diazomethane 

 upon it. The bleaching powder method was the one used to make the 

 chloramide, but it always contained some of the dichloride, which was 

 then converted into the monochloride by dissolving in caustic soda and 

 reprecipitating it with acetic acid. As the least excess of acid decom- 

 poses it completely, the yields are very poor. A small amount of the 

 substance, about 90 per cent. pure, was methylated as described above. 



