Oxamide, hydrolysis compounds

It follows from the above that the explosive power of the compound is similar to that of TNT. The fact that it readily undergoes hydrolysis, forming picric acid and oxamide is a serious drawback and prevents its use as au explosive. 

Hydrolysis of compound (87) gives 3,4-diamino-l,2,5-thiadiazole, oxamide and sulfur. In dilute ammonium hydroxide the yield of 3,4-diamino-1,2,5-thiadiazole is almost quantitative (75JOC2749). 

The salts 28 and 29 (Y = NOg) were rapidly cleaved by aqueous base to the corresponding imidazolidones and iV-formyl compounds in high yield (equation 25) °. Had addition of a second hydroxide ion and double ring opening occurred in analogy to the strong-base hydrolysis of 5 (equation 12), an oxamide would have been formed. The lack of competition from this process may be attributable to base catalysis of the fragmentation of 86, a possibility which does not exist... 

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