Ethanol → HCID 21162417, compound

HRID 894004Notes

Reaction equation

HRID 894004 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[CH2:9][C:10](=[O:23])[C:11]3[CH:17]=[C:16]([CH:18]([CH3:22])[C:19](N)=[O:20])[CH:15]=[CH:14][C:12]=3[S:13][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:8]2[CH2:9][C:10](=[O:23])[C:11]3[CH:17]=[C:16]([CH:18]([CH3:22])[C:19]([OH:26])=[O:20])[CH:15]=[CH:14][C:12]=3[S:13][C:7]=2[CH:6]=[CH:5][CH:4]=1

Participants

5

Reactant 3

HCID 702EthanolHCID 14797Potassium HydroxideHCID 12895875HCID 12895875, compound

Product 1

HCID 21162417HCID 21162417, compoundYield 27%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
85 °C

Procedure

To a mixture of 180 mg of 2-(10,11-dihydro-9-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 5 ml of ethanol was added 700 mg of potassium hydroxide in 5 ml of water, and the resulting mixture was stirred at 75° C. for 1 hour and further at 85° C. for 2 hours. The solvent or ethanol was removed by distillation to obtain a mixture, to which was added water, and the resulting mixture washed with chloroform. 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 a red oily substance, which was chromatographed over 3 g of silica gel and eluted with chloroform, thereby obtaining 48 mg (yield: 27%) of 2-(10,11-dihydro-9-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a yellow oily substance.

Workup

  1. customThe solvent or ethanol was removed by distillation
  2. customto obtain a mixture
  3. washthe resulting mixture washed with chloroform
  4. extractionextracted with ethyl acetate
  5. washThe extract was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain a red oily substance, which
  9. customwas chromatographed over 3 g of silica gel
  10. washeluted with chloroform

Sources & evidence

ORD record
ord-2f321bbb59604b60ab6482690fb72a8f
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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