Hydrochloric Acid → HCID 20338068, compound

HRID 1395750Notes

Reaction equation

HRID 1395750 reaction equation
[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:23])[C:18]([O:20]CC)=[O:19])[CH:15]=[CH:16][C:3]1=2.C(O)C.[OH-].[K+].Cl>O>[O:1]=[C:2]1[CH2:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[S:5][C:4]2[CH:13]=[C:14]([CH:17]([CH3:23])[C:18]([OH:20])=[O:19])[CH:15]=[CH:16][C:3]1=2

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 702EthanolHCID 14797Potassium HydroxideHCID 20338088HCID 20338088, compound

Product 1

HCID 20338068HCID 20338068, compoundYield 77.8%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The mixture of 83 mg of ethyl 2-(10,11-dihydro-11-oxo dibenzo[b,f]thiepin-3-yl)-propionate, 0.8 ml of ethanol, 120 mg of potassium hydroxide and 0.8 ml of water was stirred at room temperature for 2 hours. The solvent was distilled off to obtain the residue, which was acidified with hydrochloric acid and the resulting mixture was extracted with ethyl acetate. The extract was washed with saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain brown oil, which was chromatographed over silica gel, eluted with chloroform to give 59 mg of 2-(10,11-dihydro-11-oxo dibenzo[b,f]thiepin-3-yl)-propionic acid as pale yellow oil. The result in IR spectrum thereof is in accordance with that of the compound obtained in Example 9.

Workup

  1. distillationThe solvent was distilled off
  2. customto obtain the residue, which
  3. extractionthe resulting mixture was extracted with ethyl acetate
  4. washThe extract was washed with saturated sodium chloride solution
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was distilled off
  7. customto obtain brown oil, which
  8. customwas chromatographed over silica gel
  9. washeluted with chloroform

Sources & evidence

ORD record
ord-06c8c54d22ca49eaaebcf3f0a8e8b426
Source dataset
uspto-grants-1980_05
Patent number
US04205170

Reaction notes

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