Potassium Carbonate → HCID 21696505, compound

HRID 1631865Notes

Reaction equation

HRID 1631865 reaction equation
[OH:1][C:2]1[CH:15]=[CH:14][C:13]2[S:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5](=[O:16])[C:4]=2[CH:3]=1.C([O-])([O-])=O.[K+].[K+].Cl[CH2:24][CH2:25][C:26](Cl)=[O:27]>CC(C)=O>[O:16]=[C:5]1[C:4]2[CH:3]=[C:2]([O:1][C:26](=[O:27])[CH:25]=[CH2:24])[CH:15]=[CH:14][C:13]=2[S:12][C:11]2[C:6]1=[CH:7][CH:8]=[CH:9][CH:10]=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 693643-Chloropropionyl chlorideHCID 97945682-Hydroxy-9H-thioxanthen-9-one

Product 1

HCID 21696505HCID 21696505, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

5 g (22 mmol) 2-hydroxy-9H-thioxanthen-9-one was dissolved in 100 acetone. 50 mg BHT, 10.6 g 77 (mmol) K2CO3 and 5.6 g (44 mmol) 3-chloropropionyl chloride were added. The mixture was refluxed for 3 hours. The salts were removed by filtration after cooling down to room temperature and the solvent was removed under reduced pressure. The residue was treated with 100 ml water and the crude 2-propenoic acid 9-oxo-9H-thioxanthen-2-yl ester was isolated by filtration. 2-propenoic acid 9-oxo-9H-thioxanthen-2-yl ester was further purified using preparative column chromatography on a Prochrom LC80 column, using Kromasil Si 60A 10μ as silica and methylene chloride as eluent at a flow rate of 150 ml/min. 1.16 g of 2-propenoic acid 9-oxo-9H-thioxanthen-2-yl ester (19%) was isolated. The isolated compound had a purity of 99%. This analysis was confirmed by 1H-NMR spectroscopy.

Workup

  1. temperatureThe mixture was refluxed for 3 hours
  2. customThe salts were removed by filtration
  3. customthe solvent was removed under reduced pressure
  4. additionThe residue was treated with 100 ml water
  5. customthe crude 2-propenoic acid 9-oxo-9H-thioxanthen-2-yl ester was isolated by filtration
  6. custom2-propenoic acid 9-oxo-9H-thioxanthen-2-yl ester was further purified

Sources & evidence

ORD record
ord-22cc85e963c549f294cd2639de468fd5
Source dataset
uspto-grants-2014_07
Patent number
US08791289B2

Reaction notes

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