Reaction Preparation of a Diazoamido-Compound

If one molecule of a diazo-compound is allowed to act on one molecule of a primary amine, the acid radical of the former unites with the hydrogen atom of the latter, upon which the organic residues combine, as in the formation of the azo dyes. In this case, an amido-hydrogen atom is eliminated, so that a compound containing a chain of three nitrogen atoms is formed in the formation of an azo dye, one of the benzene-hydrogen atoms of the amine is eliminated  

Mixed diazo-compounds may also be prepared by causing the diazoderivative of an amine to combine with another amine  

Diazo-compounds combine only with the free amines to form diazo-amido compounds , the object of the addition of sodium acetate at the end of the reaction (see above) is to set free the base from aniline hydrochloride. 

The diazoamido-compounds are yellow substances which do not dissolve in acids. They are far more stable than the diazo-compounds, and may be recrystallised without decomposition. Still, if they are heated rapidly they puff up suddenly and decompose. In their reactions they behave like a mixture of a diazo-compound and an amine. If, e.g., they are boiled with hydrochloric add, they decompose with evolution of nitrogen, and form a phenol and an amine  

On heating with cuprous chloride and hydrochloric add, the Sand-meyer reaction takes place  

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