Aniline → 1-(4-bromophenyl)-4-phenylazo-1H-pyrazole-3,5-diamine

HRID 2095144Notes

Reaction equation

HRID 2095144 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.Cl.[Br:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][NH2:35])=[CH:30][CH:29]=1.[OH-].[Na+]>>[Br:27][C:28]1[CH:33]=[CH:32][C:31]([N:34]2[C:10]([NH2:11])=[C:9]([N:8]=[N:7][C:1]3[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=3)[C:12]([NH2:13])=[N:35]2)=[CH:30][CH:29]=1

Participants

6

Reactant 5

HCID 6115AnilineHCID 8010MalononitrileHCID 121574-Bromophenylhydrazine hydrochlorideHCID 14798Sodium HydroxideHCID 67541Carbonyl cyanide phenylhydrazone

Product 1

HCID 1354434341-(4-bromophenyl)-4-phenylazo-1H-pyrazole-3,5-diamine

Procedure

1-(4-bromophenyl)-4-phenylazo-1H-pyrazole-3,5-diamine 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 4-bromophenylhydrazine hydrochloride (112 mg, 0.5 mmol) with the addition of 0.5 mL of 5% sodium hydroxide solution. 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 49 mg (27%) of the compound as a brown 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-611bae5a1113428aba2878ebb6f4f27a
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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