Malononitrile → HCID 178509183, compound

HRID 2304422Notes

Reaction equation

HRID 2304422 reaction equation
[F:1][C:2]([F:17])([F:16])[C:3]1[CH:8]=[CH:7][C:6]([NH:9][N:10]=[C:11]([C:14]#[N:15])[C:12]#[N:13])=[CH:5][CH:4]=1.FC(F)(F)C1C=CC(N)=CC=1.C(#N)CC#N.O.[NH2:35][NH2:36]>>[NH2:15][C:14]1[C:11](=[N:10][NH:9][C:6]2[CH:7]=[CH:8][C:3]([C:2]([F:1])([F:16])[F:17])=[CH:4][CH:5]=2)[C:12]([NH2:13])=[N:36][N:35]=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, compoundYield 50%

Conditions

Temperature
75 °C

Procedure

This compound 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) as described in Example 8, 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 room 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 title 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. customThis compound was prepared
  2. customNo precipitate had formed
  3. temperatureto cool to room temperature
  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-293a6b443fef42fa944e889b3abc34b6
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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