p-Toluenesulfonic acid → HCID 2751201, compound

HRID 1268884Notes

Reaction equation

HRID 1268884 reaction equation
[C:1]([CH2:4][C:5](=[O:7])[CH3:6])(=O)[CH3:2].[CH3:8][C:9]1[CH:10]=[C:11]([CH:13]=[CH:14][CH:15]=1)[NH2:12].C1(C)C=CC(S(O)(=O)=O)=CC=1>C1(C)C=CC=CC=1>[CH3:8][C:9]1[CH:10]=[C:11]([NH:12][C:1]([CH3:2])=[CH:4][C:5](=[O:7])[CH3:6])[CH:13]=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6101p-Toluenesulfonic acidHCID 7934m-ToluidineHCID 31261Acetylacetone

Product 1

HCID 2751201HCID 2751201, compound

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

23.36 g (233 mmol) Acetylacetone, 5.00 g (47 mmol) 3-methylaniline, and 0.8 g (4.7 mmol) 4-toluenesulfonic acid are dissolved in 50 ml toluene. The reaction mixture is refluxed overnight with a Dean-Stark trap to remove water. After cooling down to room temperature, the solvent is removed in vacuo and the residue is purified by column chromatography on silica with cyclohexane/ethylacetate 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/ethylacetate

Sources & evidence

ORD record
ord-f47ba2da2fdb486fa4cb6bbfda226b16
Source dataset
uspto-grants-2007_04
Patent number
US07199136B2

Reaction notes

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