Toluamides, hydrolysis

Procarbazine Hydrochloride, USP. Procarbazine hydrochloride, Malulane. MIH. NSC-77213, N-isopropyl-o-(2-methylhydrazine)-p-toluamide. is prepared from N-iso-propyl-/>-toluamide in a process involving condensation with diethyl azodicarboxylate. methylation with methyl itxlide and base, and acid hydrolysis. Although soluble in water, it is unstable in solution. Capsules containing the equivalent of SO mg of procarbazine as its hydrochloride ore supplied. 

The active ingredient in many insect repellents is N.N-diethyl-m-toluamide. Draw the structure of this compound. Which carboxylic acid and amine would be released by hydrolysis of this compound ... 

One of the most successful mosquito repellents has the following structure and name. What are the products of the basic hydrolysis of A, A-diethyl-m-toluamide ... 

Because of its close relationship to the chemistry of peptides, the hydrolysis of amides has been the subject of extensive experimental and theoretical investigation. Observations of 0 exchange accompanying the basic hydrolysis of amides such as 1°, 2°, or 3° toluamides suggested that a tetrahedral intermediate (TI) is formed along the reaction path (Figure 7.28). ... 

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