Aniline → (3,5-Diamino-4-phenylazopyrazol-1-yl)phenylmethanone

HRID 2304443Notes

Reaction equation

HRID 2304443 reaction equation
[C:1]1([NH:7][N:8]=[C:9]([C:12]#[N:13])[C:10]#[N:11])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.NC1C=CC=CC=1.C(#N)CC#N.[C:26]([NH:34][NH2:35])(=[O:33])[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>>[NH2:11][C:10]1[C:9]([N:8]=[N:7][C:1]2[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=2)=[C:12]([NH2:13])[N:34]([C:26]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)=[O:33])[N:35]=1

Participants

5

Reactant 4

HCID 6115AnilineHCID 8010MalononitrileHCID 11955BenzoylhydrazineHCID 67541Carbonyl cyanide phenylhydrazone

Product 1

HCID 135418217(3,5-Diamino-4-phenylazopyrazol-1-yl)phenylmethanoneYield 13.1%

Procedure

This compound was prepared using 85 mg (0.5 mmol) of 2-(phenyl-hydrazono)-malononitrile, which was derived from aniline (10 mL, 107 mmol) and malononitrile (161 mmol) as described in Example 8, and benzoic hydrazide (68 mg, 0.5 mmol). Solids had not formed after heating the reaction at 75° C. for 3 hrs, however, analysis of the reaction solution by TLC indicated that no starting material remained. The solution was allowed to cool to room temperature and the solvent was evaporated. The residue was dissolved in methanol and then precipitated by the addition of water. The resulting solid was isolated by filtration and dried to yield 20 mg (13%) of the title compound as an orange coloured solid.

Workup

  1. customThis compound was prepared
  2. customSolids had not formed
  3. temperatureafter heating
  4. customthe reaction at 75° C. for 3 hrs
  5. customthe solvent was evaporated
  6. dissolutionThe residue was dissolved in methanol
  7. customprecipitated by the addition of water
  8. customThe resulting solid was isolated by filtration
  9. customdried

Sources & evidence

ORD record
ord-91602f59652444d39dadeedc77bfa00f
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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