P-Acetamidobenzene sulfonyl

The reactions of the completely reduced compounds have attracted much attention because of their close relationship to piperazine. Thus it has been shown, as might be expected, that the 2-position in compounds such as the parent 100 can be readily acetylated and benzoylated" and ureas are formed with phenylisocyanate and phenylisothiocyanate." Compound 100 also reacts at the 2-position with p-acetamidobenzene-sulfonyl chloride to give a sulfonamide. There are several examples of the alkylation of the amine in the 2-position. Various alkyl halides -have been used, as well as ethylene oxide," p-nitrobenzoyl-ethyleneimine, " and l-guanyl-3,5-dimethylpyrazole nitrate. Compound 100 also undergoes the Eschweiler-Clarke modification of the Leuckart reaction to give the 2-methyl compound." ... 

The polyvinylamine prepared by the Dynapol group has been functionalized with p-acetamidobenzene sulfonyl chloride and the sulfonamide adduct has been diazotized after deacetylation. 

The intermediate sulfonyl chloride is converted to p-acetamidobenzene-sulfon-amide by a reaction with aqueous ammonia (Step 2). Excess ammonia neutralizes the hydrogen chloride produced. The only side reaction is the hydrolysis of the sulfonyl chloride to p-acetamidobenzenesulfonic acid. 

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