Water → HCID 57285646, compound

HRID 610769Notes

Reaction equation

HRID 610769 reaction equation
S(OOS([O-])(=O)=O)([O-])(=O)=O.[K+].[K+].C([O-])(O)=[O:14].[Na+].C(#N)C.Cl.[NH2:22][C:23]12[CH:30]3[CH:25]4[C:26]5(N)[CH:29]3[CH:28]1[CH:27]5[CH:24]24.[OH2:32]>CC(C)=O>[N+:22]([C:23]12[CH:30]3[CH:25]4[CH:26]5[CH:29]3[CH:28]1[CH:27]5[CH:24]24)([O-:14])=[O:32]

Participants

7

Reactant 5

HCID 962Water2×HCID 6342AcetonitrileHCID 24412Potassium PersulfateHCID 516892Sodium BicarbonateHCID 19601788HCID 19601788, compound

Product 1

HCID 57285646HCID 57285646, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
0 °C

Procedure

Potassium monopersulfate (3.0 g), NaHCO3 (1.0 g), water (20 ml), and acetonitrile, (20 ml) were mixed together to form a first solution. A second solution of 1,4-diaminocubane hydrochloride in water, 100 mg in 25 ml, was slowly added to the first solution and the solution was cooled to 0 degrees C. Then, ozone was slowly bubbled through the solution. The reaction mixture turned milky white after one hour. The ozone was stopped and the mixture was stirred overnight. The reaction product was filtered and the filtrate was concentrated on a rotary evaporator. The concentrate was extracted twice with ethyl acetate (2×50 ml) and washed with aqueous HCl and then with brine. H NMR identified a 1,4-dinitrocubane product. Similar results are obtained when acetone is used in place of acetonitrile.

Workup

  1. customto form a first solution
  2. customThen, ozone was slowly bubbled through the solution
  3. filtrationThe reaction product was filtered
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. extractionThe concentrate was extracted twice with ethyl acetate (2×50 ml)
  6. washwashed with aqueous HCl
  7. customSimilar results

Sources & evidence

ORD record
ord-e056c2ec00e14cb487369a8365ca7a06
Source dataset
uspto-grants-1999_12
Patent number
US05998661

Reaction notes

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