Acetic Acid → HCID 12895869, compound

HRID 894000Notes

Reaction equation

HRID 894000 reaction equation
[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:20])[C:17](N)=[O:18])=[CH:15][C:9]=3[C:8](=[O:21])[CH2:7][C:6]=2[CH:22]=1.C(O)(=[O:25])C.Br>CCCCCC>[F:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][C:10]3[CH:12]=[CH:13][C:14]([CH:16]([CH3:20])[C:17]([OH:25])=[O:18])=[CH:15][C:9]=3[C:8](=[O:21])[CH2:7][C:6]=2[CH:22]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 12895868HCID 12895868, compound

Product 1

HCID 12895869HCID 12895869, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

To a mixture of 150 mg of 2-(10,11-dihydro-8-fluoro-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 1.5 ml of acetic acid was added 1.5 ml of hydrobromic acid, and the mixture was refluxed with stirring for 1 hour. To this was added ice water, and the resulting mixture was 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 brown crystals, which were chromatographed over 10 g of silica gel and eluted with chloroform/methanol (50/1). The thus obtained product was recrystallized from ethyl acetate--n-hexane to give 105 mg (yield: 70%) of 2-(10,11-dihydro-8-fluoro-11-oxodibenzo[b,f]-thiepin-2-yl)-propionic acid as light yellow crystals having a melting point of 213°-214° C.

Workup

  1. temperaturethe mixture was refluxed
  2. extractionthe resulting mixture was extracted with ethyl acetate
  3. washThe extract was washed with a saturated sodium chloride solution
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationThe solvent was distilled off
  6. customto obtain brown crystals, which
  7. customwere chromatographed over 10 g of silica gel
  8. washeluted with chloroform/methanol (50/1)
  9. customThe thus obtained product was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-9149e47ad6eb4faba27134f40416f9c8
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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