Hydrochloric Acid → HCID 21162410, compound

HRID 893996Notes

Reaction equation

HRID 893996 reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19](N)=[O:20])=[CH:17][C:11]=3[C:10](=[O:23])[CH2:9][C:8]=2[CH:24]=1)[CH3:2].[OH-:25].[Na+].O.Cl>C(O)C>[CH2:1]([O:3][C:4]1[CH:5]=[CH:6][C:7]2[S:13][C:12]3[CH:14]=[CH:15][C:16]([CH:18]([CH3:22])[C:19]([OH:25])=[O:20])=[CH:17][C:11]=3[C:10](=[O:23])[CH2:9][C:8]=2[CH:24]=1)[CH3:2]

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 12895861HCID 12895861, compound

Product 1

HCID 21162410HCID 21162410, compoundYield 37%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 70 mg of 2-(10,11-dihydro-8-ethoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide, 800 mg of sodium hydroxide, 5 ml of water and 5 ml of ethanol was refluxed for 3 hours. After the completion of the reaction, the solvent was removed by distillation to obtain a residue, to which was added ice water, and the mixture was acidified with 10% hydrochloric acid and extracted with chloroform. The extract was washed with water and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain a residue, which was chromatographed over silica gel and eluted with chloroform/benzene (4/1), thereby obtaining 26 mg (yield: 37%) of 2-(10,11-dihydro-8-ethoxy-11-oxodibenzo-[b,f]thiepin-2-yl)-propionic acid as an oil.

Workup

  1. temperaturewas refluxed for 3 hours
  2. customAfter the completion of the reaction
  3. customthe solvent was removed by distillation
  4. customto obtain a residue
  5. extractionextracted with chloroform
  6. washThe extract was washed with water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationThe solvent was distilled off
  9. customto obtain a residue, which
  10. customwas chromatographed over silica gel
  11. washeluted with chloroform/benzene (4/1)

Sources & evidence

ORD record
ord-d7d4428f36b742d889a1a9f77d95abf1
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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