Ethanol → Zaltoprofen

HRID 1390120Notes

Reaction equation

HRID 1390120 reaction equation
[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:4]=2[CH2:3]1.C([OH:24])C.[OH-].[K+]>O>[O:1]=[C:2]1[C:8]2[CH:9]=[CH:10][CH:11]=[CH:12][C:7]=2[S:6][C:5]2[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([OH:24])=[O:19])=[CH:16][C:4]=2[CH2:3]1

Participants

5

Reactant 3

HCID 702Ethanol2×HCID 14797Potassium HydroxideHCID 20295009HCID 20295009, compound

Product 1

HCID 5720ZaltoprofenYield 64%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 150 mg of 2-(10,11-dihydro-10-oxodibenzo[b,f]-thiepin-2-yl)-propionamide and 2 ml of ethanol was added 400 mg of potassium hydroxide in 2 ml of water, and the mixture was refluxed with stirring for 6 hours. After the completion of the reaction, ethanol was removed by distillation to obtain a residue to which was added water. The residue was washed with ethyl acetate, and an alkaline layer was acidified with hydrochloric acid and extracted with ethyl acetate. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was removed by distillation to obtain a brown oil substance, which was chromatographed over 4 g of silica gel and eluted with benzene-chloroform (1:1) to obtain a light yellow oil substance. This substance was recrystallized from benzene-n-hexane, thereby obtaining 96 mg (yield: 64%) of 2-(10,11-dihydro-10-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as pale yellow crystals having a melting point of 130.5°-131.5° C.

Workup

  1. temperaturethe mixture was refluxed
  2. customwas removed by distillation
  3. customto obtain a residue to which
  4. washThe residue was washed with ethyl acetate
  5. extractionextracted with ethyl acetate
  6. washThe extract was washed with a saturated sodium chloride solution
  7. dry with materialdried over anhydrous sodium sulfate
  8. customThe solvent was removed by distillation
  9. customto obtain a brown oil substance, which
  10. customwas chromatographed over 4 g of silica gel
  11. washeluted with benzene-chloroform (1:1)
  12. customto obtain a light yellow oil substance
  13. customThis substance was recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-d650633f27504b69be8755a4648905c6
Source dataset
uspto-grants-1981_01
Patent number
US04247706

Reaction notes

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