Acetylacetone → HCID 577984, compound

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This invention is a method of making 3,6-diamino-1,2,4,5,-tetrazine (compound 5, DATZ). Triaminoguanidine monohydrochloride (compound 1) in water solution is combined with 2,4-pentanedione (compound 2) to form a precipitate comprised of 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2-dihydro-1,2,4,5-tetrazine (compound 3). A mixture of compound 3 in a suitable solvent is contacted with nitric oxide (NO) or nitrogen dioxide (NO2) to form 3,6-bis(3,5-dimethylpyrazol-1-yl)-1,2,4,5-tetrazine (compound 4). The NO or NO2 is then removed from the mixture by passing an inert gas through the mixture or, alternatively, compound 4 is separated from the mixture and mixed with fresh solvent to form a mixture free of NO and NO2. The mixture is contacted with ammonia (NH3), first at a temperature below about 35 C and then at a temperature above about 50 C, to form 3,6-diamino-1,2,4,5-tetrazine and 3,5-dimethyl-lH-pyrazole (compound 7). A preferred solvent is 1-methyl-2-pyrrolidinone (NMP).

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