Ethanol → HCID 21162419, compound

HRID 894005Notes

Reaction equation

HRID 894005 reaction equation
[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][C:8](=[O:21])[C:9]3[CH:15]=[C:14]([CH:16]([CH3:20])[C:17](N)=[O:18])[CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1.C([OH:26])C.[OH-].[K+]>O>[CH3:1][O:2][C:3]1[CH:23]=[CH:22][C:6]2[CH2:7][C:8](=[O:21])[C:9]3[CH:15]=[C:14]([CH:16]([CH3:20])[C:17]([OH:26])=[O:18])[CH:13]=[CH:12][C:10]=3[S:11][C:5]=2[CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12895876HCID 12895876, compound

Product 1

HCID 21162419HCID 21162419, compoundYield 33%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

To a mixture of 393 mg of 2-(10,11-dihydro-7-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 12 ml of ethanol was added 1.2 g of potassium hydroxide in 3 ml of water, and the mixture was refluxed with stirring for 7.5 hours. The solvent or ethanol was removed by distillation to obtain a mixture, to which was added water, and the resulting 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 distilled off to obtain an orange oil, which was chromatographed over 10 g of silica gel and eluted with chloroform, thereby obtaining 138 mg (yield: 33%) of 2-(10,11-dihydro-7-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a light yellow oil.

Workup

  1. temperaturethe mixture was refluxed
  2. customThe solvent or ethanol was removed by distillation
  3. customto obtain a mixture
  4. washthe resulting 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. distillationThe solvent was distilled off
  9. customto obtain an orange oil, which
  10. customwas chromatographed over 10 g of silica gel
  11. washeluted with chloroform

Sources & evidence

ORD record
ord-3dddcbb0d906469d835a869209439452
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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