Malononitrile → HCID 178493283, compound

HRID 2304439Notes

Reaction equation

HRID 2304439 reaction equation
CO[C:3]1[CH:4]=[C:5]([NH:13][N:14]=[C:15]([C:18]#[N:19])[C:16]#[N:17])[CH:6]=[C:7]([C:9]([F:12])([F:11])[F:10])[CH:8]=1.[CH3:20]OC1C=C(C=C(C(F)(F)F)C=1)N.C(#N)CC#N.[OH2:38].[NH2:39][NH2:40]>>[NH2:19][C:18]1[C:15](=[N:14][NH:13][C:5]2[CH:6]=[C:7]([C:9]([F:10])([F:11])[F:12])[CH:8]=[C:3]([O:38][CH3:20])[CH:4]=2)[C:16]([NH2:17])=[N:40][N:39]=1

Participants

5

Reactant 4

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

Product 1

HCID 178493283HCID 178493283, compoundYield 7%

Procedure

This compound 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) as described in Example 8, 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 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 10 mg (7%) of the title compound as a yellow solid.

Workup

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

Sources & evidence

ORD record
ord-c34cf1fb5fcc4a0098f31f6faa6f3e69
Source dataset
uspto-grants-2002_08
Patent number
US06436915B1

Reaction notes

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