Acetylacetone → HCID 577984, compound

HRID 1198722Notes

Reaction equation

HRID 1198722 reaction equation
NC1N=NC(N)=NN=1.Cl.NN=C(N)N(N)N.CC(=O)CC(=O)C.[CH3:24][C:25]1[CH:29]=[C:28]([CH3:30])[N:27]([C:31]2[NH:32][NH:33][C:34]([N:37]3[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[N:38]3)=[N:35][N:36]=2)[N:26]=1.[N]=O.[N+]([O-])=O>O>[CH3:24][C:25]1[CH:29]=[C:28]([CH3:30])[N:27]([C:31]2[N:32]=[N:33][C:34]([N:37]3[C:41]([CH3:42])=[CH:40][C:39]([CH3:43])=[N:38]3)=[N:35][N:36]=2)[N:26]=1

Participants

8

Reactant 6

HCID 31261Acetylacetone2×HCID 145068Nitric OxideHCID 2833791,2,4,5-Tetrazine-3,6-diamine2×HCID 73462575HCID 73462575, compound2×HCID 178426375HCID 178426375, compound3×HCID 178526396Nitrogen Dioxide

Product 1

HCID 577984HCID 577984, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

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).

Workup

  1. customto form a precipitate

Sources & evidence

ORD record
ord-d3e2ebe7786f4126aac2a6ffe6d41302
Source dataset
uspto-grants-1994_01
Patent number
US05281706

Reaction notes

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