Acetic Acid → 3-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

HRID 639137Notes

Reaction equation

HRID 639137 reaction equation
[CH3:1]/[C:2](/[NH2:6])=[CH:3]\[C:4]#[N:5].[F:7][C:8]([F:17])([F:16])[C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)N.C(O)(=O)C>O>[F:7][C:8]([F:17])([F:16])[C:9]1[CH:15]=[C:14]([NH:6][C:2]([CH3:1])=[CH:3][C:4]#[N:5])[CH:13]=[CH:11][CH:10]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 73753-(Trifluoromethyl)anilineHCID 53247203-Aminocrotonitrile

Product 1

HCID 50752873-{[3-(Trifluoromethyl)phenyl]amino}but-2-enenitrile

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

3-Aminocrotonitrile (1.0 g, 12.2 mmol), 3-trifluoromethylaniline (2.0 g, 12.4 mmol), and acetic acid (1.23 g, 20.5 mmol) are dissolved in water (8 ml). The reaction mixture is stirred at room temperature for 30 minutes. The mixture is extracted with toluene three times and the organic phase is dried over sodium sulfate. The solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethyl acetate mixtures as eluent.

Workup

  1. extractionThe mixture is extracted with toluene three times
  2. dry with materialthe organic phase is dried over sodium sulfate
  3. customThe solvent is removed in vacuo
  4. customthe residue is purified by column chromatography on silica with cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-69ed2ddc8d2e4441bbae1fdfc04adc7b
Source dataset
uspto-grants-2010_04
Patent number
US07691854B2

Reaction notes

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