Hydrochloric Acid → HCID 12895860, compound

HRID 893995Notes

Reaction equation

HRID 893995 reaction equation
[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18](N)=[O:19])=[CH:16][C:10]=3[C:9](=[O:22])[CH2:8][C:7]=2[CH:23]=1.[OH-:24].[Na+].O.Cl>C(O)C>[CH3:1][O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12][C:11]3[CH:13]=[CH:14][C:15]([CH:17]([CH3:21])[C:18]([OH:24])=[O:19])=[CH:16][C:10]=3[C:9](=[O:22])[CH2:8][C:7]=2[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 14798Sodium HydroxideHCID 12895859HCID 12895859, compound

Product 1

HCID 12895860HCID 12895860, compoundYield 35%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture of 0.1 g of 2-(10,11-dihydro-8-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide, 1.0 g of sodium hydroxide, 10 ml of water and 20 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 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 a solid substance. This substance was recrystallized from benzene-n-hexane to give 35 mg (yield: 35%) of 2-(10,11-dihydro-8-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a powder having a melting point of 152°-153° C.

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)
  12. customobtaining a solid substance
  13. customThis substance was recrystallized from benzene-n-hexane

Sources & evidence

ORD record
ord-a9949b5e4b164c22b17ebfe948597043
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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