Malononitrile → HCID 178493283, compound

HRID 254971Notes

Reaction equation

HRID 254971 reaction equation
COC1C=C(N[N:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])C=C(C(F)(F)F)C=1.[CH3:20][O:21][C:22]1[CH:23]=[C:24]([CH:26]=[C:27]([C:29]([F:32])([F:31])[F:30])[CH:28]=1)[NH2:25].C(#N)CC#N.O.[NH2:39][NH2:40]>>[CH3:20][O:21][C:22]1[CH:23]=[C:24]([NH:25][N:14]=[C:15]2[C:16]([NH2:17])=[N:40][N:39]=[C:18]2[NH2:19])[CH:26]=[C:27]([C:29]([F:30])([F:31])[F:32])[CH:28]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 24654Hydrazine hydrate (1:1)HCID 6056715-(Trifluoromethyl)-m-anisidineHCID 21954979HCID 21954979, compound

Product 1

HCID 178493283HCID 178493283, compound

Procedure

4-[(3-methoxy-5-trifluoromethylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 134 mg (0.5 mmol) of 2-[(3-methoxy-5-trifluoromethylphenyl)hydrazono]malononitrile, which was derived from 3-methoxy-5-trifluoromethylaniline (191 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 10 mg (7%) of the compound as a yellow 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-54e117262164483d8357f3e7a872ffc2
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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