Acetic Acid → HCID 11345909, compound

HRID 1935711Notes

Reaction equation

HRID 1935711 reaction equation
[N+:1]([C:4]1[C:8]([N:9]=[N:10][C:11]2[C:12]([N+:16]([O-:18])=[O:17])=[N:13][O:14][N:15]=2)=[N:7][O:6][N:5]=1)([O-:3])=[O:2].C(O)(=O)C>CO.[Zn]>[N+:1]([C:4]1[C:8]([NH:9][NH:10][C:11]2[C:12]([N+:16]([O-:18])=[O:17])=[N:13][O:14][N:15]=2)=[N:7][O:6][N:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 2

HCID 176Acetic AcidHCID 3111103HCID 3111103, compound

Product 1

HCID 11345909HCID 11345909, compoundYield 100%

Reagents, catalysts & solvents 2

HCID 23994ZincCatalystHCID 887MethanolSolvent

Procedure

To a suspension of 3,3′-dinitro-4,4′-azofurazan (1.42 g, 6.0 mmol) and Zn (0.78 g, 12 mmol) in 10 ml of methanol at room temperature, was added dropwise glacial acetic acid (0.8 ml, 12 mmol). A vigorous reaction took place, and after the greenish reaction mixture was stirred at room temperature for 2 hours. The slurry was filtered through a bed of celite and the filtrate was concentrated on a rotary evaporator and passed through a bed of silica gel using CH2Cl2/EtOAc. Removal of solvent gave 1.46 g (100% yield, one spot by TLC) of 3,3′-dinitro-4,4′-hydrazofurazan, a pale yellow solid, 1H NMR(DMSO-d6); δ9.98 (s) ppm. Recrystallization from chloroform/acetone gave 1.26 g of 3,3′-dinitro-4,4′-hydrazofurazan, mp 171-173° C.

Workup

  1. customA vigorous reaction
  2. customafter the greenish reaction mixture
  3. filtrationThe slurry was filtered through a bed of celite
  4. concentrationthe filtrate was concentrated on a rotary evaporator
  5. customRemoval of solvent

Sources & evidence

ORD record
ord-f562ac581cea44e69f7fe92a5fa9627e
Source dataset
uspto-grants-2002_05
Patent number
US06388087B1

Reaction notes

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