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

HRID 2095143Notes

Reaction equation

HRID 2095143 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)phenylmethanone

Procedure

(3,5-diamino-4-phenylazopyrazol-1-yl)phenylmethanone was prepared using 85 mg (0.5 mmol) of 2-(phenylhydrazono)malononitrile, which was derived from aniline (10 mL, 107 mmol) and malononitrile (161 mmol), 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 ambient 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 compound as an orange coloured solid.

Workup

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

Sources & evidence

ORD record
ord-4847e282abae49e38f3f15e6a75a864c
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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