Hydrogen Peroxide → HCID 10016333, compound

HRID 465333Notes

Reaction equation

[N+:1](C1C=C2C(=CC=1)N1N=NN=C1C=N2)([O-:3])=[O:2].OO.[N+:19]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][CH:31]=1)[N:28]1[N:32]=[N:33][N:34]=[C:27]1[C:26](=[O:35])[NH:25]2)([O-:21])=[O:20].OS(O)(=O)=O.[N+]([O-])([O-])=O.[K+]>O.CC(O)=O>[N+:19]([C:22]1[CH:23]=[C:24]2[C:29](=[CH:30][C:31]=1[N+:1]([O-:3])=[O:2])[N:28]1[N:32]=[N:33][N:34]=[C:27]1[C:26](=[O:35])[NH:25]2)([O-:21])=[O:20]

Participants

Conditions

Temperature: 85 °C

Procedure

The nitrotetrazoloquinoxaline (23) (1.84 g, 8.51 mmol) was added to a mixture of 15 ml of glacial AcOH and 20 ml of 30% H2O2 and heated at 85° C. in an oil bath for 16 hours. Upon cooling, the mixture was diluted with H2O (50 ml) and the precipitate collected by filtration. Recrystallization from 40 ml of 50% aq. DMF gave 1.29 g of yellow flocculant needles comprising 7-nitrotetrazolo[1,5-a]quinoxalin-4(5H)-one (24). This nitrotetrazoloquinoxalinone (3.00 g, 12.9 mmol) was added to conc. H2SO4 (40 ml) and treated with KNO3 (1.43 g, 14.1 mmol) with warming to 50° C. under N2. The mixture was poured onto 600 ml of ice-H2O, and a light yellow solid collected by filtration and washed with H2O, yielding 7,8-dinitrotetrazolo[1,5-a]quinoxalin-4(5H)-one (25).

Workup

temperatureUpon cooling
filtrationthe precipitate collected by filtration
customRecrystallization from 40 ml of 50% aq. DMF
customgave 1.29 g of yellow flocculant needles
temperaturewith warming to 50° C. under N2
filtrationa light yellow solid collected by filtration
washwashed with H2O

Sources & evidence

ORD record: ord-3887cf5c3820452a80fa71767d5137f5
Source dataset: uspto-grants-1992_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05153196

Reaction notes

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