N-(4-Nitro-1,2,5-oxadiazol-3-yl)nitramide → HCID 18671041, compound

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Reaction Steps

A dry clean 250 ml 3 neck round bottom flask equipped with a nitrogen port, magnetic stirring bar, thermocouple was set into an ice bath. 3-Nitroamino-4-nitrofurazan (5.0 grams 0.0285M) was added with 40 ml distilled water. Hydroxyl amine (HA) (11.5% wt in water) was preweighed into a vial, (8.20 grams 0.94 grams HA; 0.0285M). HA was added over three minutes with a pipet at a temperature not exceeding 3° C. The vial was rinsed with 2 mls H2O for quantitative transfer of its contents. Following ten minutes the reaction mixture was stirred cold, then the ice bath was withdrawn and stirred at ambient for 11/2-2 hrs. After transfer to a tarred one neck flask, the water was removed in vacuo at 40° C. to obtain crystals. Crystals were then placed under high vacuum for at least 8 hrs., giving 101% theoretical yield. The product was recrystallized using 9.87 ml of nitromethane per gram of crude product nitromethane. A slurry was formed and was stirred at 63° C., then a few drops of methanol was added and all crystals went into solution. The solution was then set into a refrigerator-freezer at -20° C. for 16 hrs. Sparkly pearlescent flaky crystals were collected on paper and dried to give 84% theoretical yield. DSC: melt 132° C., exothermic decomposition 162.9° C. FTIR, 3200-2700 (m), 1582 (s), 1510 (s), 1336, 1303 (d). Empirical formula, C2H4N6O6, density, (x-ray analysis) 1.875 g/cc. ΔHc 1648 cal/g, ΔHf +18 Kcal/mole.

Provenance & Evidence