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

HRID 1766345Notes

Reaction equation

HRID 1766345 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-50e0ce564f0042a68a7262825dc5f98f
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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