Hydrogen Peroxide → 1,2,5-Oxadiazol-3-amine, 4,4'-azoxybis-

HRID 277613Notes

Reaction equation

HRID 277613 reaction equation
OO.S(=O)(=O)(O)O.[NH2:8][C:9]1[C:13]([NH2:14])=[N:12][O:11][N:10]=1.[N:15]([C:17]1[C:18]([NH2:22])=[N:19][O:20][N:21]=1)=[O:16]>>[NH2:22][C:18]1[C:17]([N+:15](=[N:14][C:13]2[C:9]([NH2:8])=[N:10][O:11][N:12]=2)[O-:16])=[N:21][O:20][N:19]=1

Participants

5

Reactant 4

HCID 784Hydrogen PeroxideHCID 1118Sulfuric AcidHCID 5376773,4-DiaminofurazanHCID 4778074HCID 4778074, compound

Product 1

HCID 5338711,2,5-Oxadiazol-3-amine, 4,4'-azoxybis-Yield 88%

Conditions

Temperature
18 °C

Procedure

This procedure was modeled from the original Russian preparation. To 30% hydrogen peroxide (100.0 g, 0.88 mol) in a 500 ml jacketed flask maintained at 18° C. was added 98% sulfuric acid (55.0 g, 0.56 mol) over 10 minutes with stirring. Then, 3,4-diaminofurazan (10.0 g, 0.10 mole) was added. The suspension was stirred for 24 hours in which time the soluble green nitroso-aminofurazan was converted to the insoluble orange DAAF. The product was filtered on a glass frit, washed with water and air dried to yield 9.29 g (88%) of crude material. For recrystallization the crude compound was dissolved in the minimum amount of room temperature DMSO (approximately 22 ml) and then water (45 ml) was added over 5 minutes with stirring. The pure DAAF was filtered, washed with water and air-dried. This material had the same properties as previously reported by the Russians. 1H NMR (deuteriomethylsulfoxide) δ 6.65 (s, 2H), 6.93 (s, 2H); 13C NMR (deuteriomethylsulfoxide) δ 148.3, 151.2, 152.6, 153.9.

Workup

  1. customThis procedure was modeled from the original Russian preparation
  2. filtrationThe product was filtered on a glass frit
  3. washwashed with water and air
  4. customdried

Sources & evidence

ORD record
ord-a780204da6b74748bf60f776551d2fe8
Source dataset
uspto-grants-2002_03
Patent number
US06358339B1

Reaction notes

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