Malononitrile → HCID 178509174, compound

HRID 254955Notes

Reaction equation

HRID 254955 reaction equation
BrC1C=CC=CC=1N[N:9]=[C:10]([C:13]#[N:14])[C:11]#[N:12].[Br:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH2:18].C(#N)CC#N.O.[NH2:29][NH2:30]>>[Br:15][C:16]1[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=1[NH:18][N:9]=[C:10]1[C:11]([NH2:12])=[N:30][N:29]=[C:13]1[NH2:14]

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 119922-BromoanilineHCID 24654Hydrazine hydrate (1:1)HCID 779795Propanedinitrile, [(2-bromophenyl)hydrazono]-

Product 1

HCID 178509174HCID 178509174, compound

Procedure

4-[(2-bromophenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 125 mg (0.5 mmol) of 2-[(2-bromophenyl)hydrazono]malononitrile, which was derived from 2-bromoaniline (172 mg, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. Very little solid had formed after heating the reaction at 75° C. for 1 hr, 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 ethyl acetate and then precipitated by the addition of hexanes. The resulting solid was isolated by filtration and dried to yield 102 mg (73%) of the compound as an orange solid.

Workup

  1. customVery little solid had formed
  2. temperatureafter heating
  3. customthe reaction at 75° C. for 1 hr
  4. customthe solvent was evaporated
  5. dissolutionThe residue was dissolved in ethyl acetate
  6. customprecipitated by the addition of hexanes
  7. customThe resulting solid was isolated by filtration
  8. customdried

Sources & evidence

ORD record
ord-a80f914ca90447ec819ca010b086c9b6
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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