p-Toluenesulfonic acid → HCID 2748650, compound

HRID 1766347Notes

Reaction equation

HRID 1766347 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[F:8][C:9]([F:18])([F:17])[C:10]1[CH:11]=[C:12]([CH:14]=[CH:15][CH:16]=1)[NH2:13].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[F:8][C:9]([F:17])([F:18])[C:10]1[CH:11]=[C:12]([NH:13][C:1]([CH3:2])=[CH:4][C:5](=[O:7])[CH3:6])[CH:14]=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 73753-(Trifluoromethyl)anilineHCID 31261Acetylacetone

Product 1

HCID 2748650HCID 2748650, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

Acetylacetone (15.53 g, 155 mmol), 3-trifluoromethylaniline (5.00 g, 31 mmol), and 4-toluenesulfonic acid (0.53 g, 3.1 mmol) are dissolved in toluene (50 ml). The reaction mixture is refluxed overnight with a Dean-Stark trap to remove water. After cooling to room temperature, 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. temperatureThe reaction mixture is refluxed overnight with a Dean-Stark trap
  2. customto remove water
  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-e2223661802845149342610288db50e6
Source dataset
uspto-grants-2007_06
Patent number
US07230017B2

Reaction notes

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