Malononitrile → HCID 178509183, compound

HRID 254952Notes

Reaction equation

HRID 254952 reaction equation
FC(F)(F)C1C=CC(N[N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])=CC=1.[F:18][C:19]([F:28])([F:27])[C:20]1[CH:26]=[CH:25][C:23]([NH2:24])=[CH:22][CH:21]=1.C(#N)CC#N.O.[NH2:35][NH2:36]>>[F:18][C:19]([F:27])([F:28])[C:20]1[CH:26]=[CH:25][C:23]([NH:24][N:10]=[C:11]2[C:12]([NH2:13])=[N:36][N:35]=[C:14]2[NH2:15])=[CH:22][CH:21]=1

Participants

5

Reactant 4

HCID 8010MalononitrileHCID 99644-(Trifluoromethyl)anilineHCID 24654Hydrazine hydrate (1:1)HCID 2781638[4-(Trifluoromethyl)phenyl]carbonohydrazonoyl dicyanide

Product 1

HCID 178509183HCID 178509183, compound

Conditions

Temperature
75 °C

Procedure

4-[(4-trifluoromethylphenyl)hydrazono]-4H-pyrazole-3,5-diamine was prepared using 119 mg (0.5 mmol) of 2-[(4-trifluoromethylphenyl)hydrazono]malononitrile, which was derived from 4-(trifluoromethyl)aniline (126 μL, 1.0 mmol) and malononitrile (1.5 mmol), and hydrazine hydrate. No precipitate had formed after heating 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 67 mg (50%) of the compound as a greenish brown solid; 1H NMR (ppm, DMSO-d6): 6.03 (br s, 2H), 6.48 (br s, 2H), 7.63 (d, 2H), 7.80 (d, 2H), 10.80 (br s, 1H).

Workup

  1. customNo precipitate had formed
  2. temperatureto cool to ambient temperature
  3. customthe solvent was evaporated
  4. dissolutionThe residue was dissolved in ethyl acetate
  5. customprecipitated by the addition of hexanes
  6. customThe resulting solid was isolated by filtration
  7. customdried

Sources & evidence

ORD record
ord-ebcc09c3b535471bb8e3edd3fb2b7b17
Source dataset
uspto-grants-2011_01
Patent number
US07875728B2

Reaction notes

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