Ethanol → HCID 12895872, compound

HRID 894002Notes

Reaction equation

HRID 894002 reaction equation
[CH3:1][O:2][C:3]1[C:13]2[S:12][C:11]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19](N)=[O:20])=[CH:17][C:10]=3[C:9](=[O:23])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1.C([OH:26])C.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[C:13]2[S:12][C:11]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19]([OH:26])=[O:20])=[CH:17][C:10]=3[C:9](=[O:23])[CH2:8][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12895871HCID 12895871, compound

Product 1

HCID 12895872HCID 12895872, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 273 mg of 2-(10,11-dihydro-6-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 8 ml of ethanol was added 800 mg of potassium hydroxide in 2 ml of water, and the resulting mixture was refluxed with stirring for 6 hours. The solvent or ethanol was distilled off to obtain a residue, to which was added water, and the mixture was washed with benzene. The aqueous 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 yellowish-brown oil, which was chromatographed over 9 g silica gel and eluted with chloroform to obtain light yellow crystals. The crystals were recrystallized from benzene-n-hexane to obtain 165 mg (yield: 60%) of 2-(10,11-dihydro-6-methoxy-11-oxodibenzo-[b,f]thiepin-2-yl)-propionic acid as light yellow crystals having a melting point of 176°-178° C.

Workup

  1. temperaturethe resulting mixture was refluxed
  2. distillationThe solvent or ethanol was distilled off
  3. customto obtain a residue
  4. washthe mixture was washed with benzene
  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 yellowish-brown oil, which
  10. customwas chromatographed over 9 g silica gel
  11. washeluted with chloroform
  12. customto obtain light yellow crystals
  13. customThe crystals were recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-3cc1edd339664fb2866ac4935f59fc97
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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