Nitric Acid → 1,4-Dinitro-1H-imidazole

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Reaction Steps

4-nitroimidazole (88 gms.) obtained from Fluka Chemical Company, Ronkonkoma, N.Y, was dissolved in glacial acetic acid (240 ml ) and acetic anhydride (120 ml). Nitric acid (98%, 80 ml. density=1.52 gm/cc) was added dropwise while continuously stirring the mixture over a period of 60 min. The mixture is then stirred at room temperature for another 3 hrs.. The mixture gradually turned into a golden yellow color solution. This solution was poured onto crushed ice, stirred for about 1 hour and filtered the precipitate. The sample was dried completely, and 85 grms. of 1,4 -dinitroimidazole was recovered having a melting point of 92° C. corresponding to the reported melting point in the literature. The structure was further confirmed by NMR (1H NMR, in CDCl3, 9.0 and 9.4 ) and Mass (M+ 158) Spectroscopy techniques.

Provenance & Evidence