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

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 Following ten minutes the reaction mixture was stirred cold, then the ice bath was withdrawn and stirred at ambient for 11/2-2 hrs.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.

1. customthermocouple was set into an ice bath
2. distillationdistilled water
3. additionHA was added over three minutes with a pipet at a temperature not
4. customexceeding 3° C
5. washThe vial was rinsed with 2 mls H2O for quantitative transfer of its contents
6. waitFollowing ten minutes
7. customthe ice bath was withdrawn
8. stirringstirred at ambient for 11/2-2 hrs
9. customAfter transfer to a tarred one neck flask, the water was removed in vacuo at 40° C.
10. customto obtain crystals
11. waitCrystals were then placed under high vacuum for at least 8 hrs
12. custom, giving 101% theoretical yield
13. customThe product was recrystallized
14. customA slurry was formed
15. stirringwas stirred at 63° C.
16. customSparkly pearlescent flaky crystals were collected on paper
17. customdried
18. customto give 84% theoretical yield
19. custommelt 132° C.
20. customexothermic decomposition 162.9° C

ORD record

ord-af8f6cc7ae79468398a65129aa492ff1

Source dataset

uspto-grants-1995_10

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US05460669