Sulfuric Acid → 1092799-06-8

HRID 2390561Notes

Reaction equation

HRID 2390561 reaction equation
[N:1]([O-:3])=[O:2].[Na+].S(=O)(=O)(O)O.N[C:11]1[NH:15][N:14]=[C:13]([N+:16]([O-:18])=[O:17])[C:12]=1[N+:19]([O-:21])=[O:20]>>[N+:1]([C:11]1[C:12]([N+:19]([O-:21])=[O:20])=[C:13]([N+:16]([O-:18])=[O:17])[NH:14][N:15]=1)([O-:3])=[O:2]

Participants

4

Reactant 3

HCID 1118Sulfuric Acid2×HCID 23668193Sodium Nitrite3×HCID 178509124HCID 178509124, compound

Product 1

HCID 577882191092799-06-8

Conditions

Temperature
20 °C

Procedure

650 mg of sodium nitrite are added rapidly at 0-10° C. to a 20% solution of sulfuric acid (5 mL) containing 145 mg of 5-amino-3,4-dinitropyrazole. The mixture is left to react at this temperature for 1 hour and then the cold mixture is poured into 40 mL of 10% strength aqueous sodium nitrite which is maintained at 20° C. The mixture is subsequently heated at 50-60° C. for 30 minutes until the effervescence disappears completely. The excess sodium nitrite is then neutralized by addition of concentrated sulfuric acid. The reaction mixture is extracted 3 times with ethyl acetate. The organic phases are combined, washed with a brine, dried over magnesium sulfate, filtered and then concentrated. 3,4,5-Trinitropyrazole is obtained in the form of an orange gum with a crude yield of 80%. The NMR and IR analyses are in accordance with those obtained with the product of Example 3.

Workup

  1. waitThe mixture is left
  2. customto react at this temperature for 1 hour
  3. temperatureThe mixture is subsequently heated at 50-60° C. for 30 minutes until the effervescence
  4. extractionThe reaction mixture is extracted 3 times with ethyl acetate
  5. washwashed with a brine
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

Sources & evidence

ORD record
ord-524e88c1eaff472d90d201d2eaf2908f
Source dataset
uspto-grants-2012_09
Patent number
US08273784B2

Reaction notes

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