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

HRID 2095146Notes

Reaction equation

HRID 2095146 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.[F:27][C:28]1[CH:33]=[CH:32][C:31]([NH:34][NH2:35])=[CH:30][CH:29]=1.[OH-].[Na+]>>[F: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 14798Sodium HydroxideHCID 67541Carbonyl cyanide phenylhydrazoneHCID 699814-Fluorophenylhydrazine hydrochloride

Product 1

HCID 1355464071-(4-fluorophenyl)-4-phenylazo-1H-pyrazole-3,5-diamine

Procedure

1-(4-fluorophenyl)-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-fluorophenylhydrazine hydrochloride (81 mg, 0.5 mmol) with the addition of 0.5 mL of 5% sodium hydroxide solution. After reacting for 4 hrs, very little solid had formed; however, analysis of the reaction solution by TLC indicated that no starting material remained. The resulting solid was removed by filtration and the solvent was evaporated from the filtrate to yield 29 mg (20%) of the compound as a brown solid.

Workup

  1. customvery little solid had formed
  2. customThe resulting solid was removed by filtration
  3. customthe solvent was evaporated from the filtrate

Sources & evidence

ORD record
ord-6fb36c63ad4e45678a9646872f92cd11
Source dataset
uspto-grants-2013_05
Patent number
US08445694B2

Reaction notes

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