Cyanogen, para preparation

The preparation of a pair of iminohydantoins invokes the addition of amide nitrogen to a cyano group for formation of the imidazole ring. The products exhibit unexpectedly quite different biological activities. Reaction of the cyanamide (92-1) from para-chloroaniline and cyanogen bromide with A-methylchloroacetamide (92-2) can be visualized to lead initially to the alkylation product (92-3). Cyclization by addition to the nitrile group then affords clazolamine (92-4) [98], a compound described as a diuretic. 

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