Acetic Acid → HCID 12895874, compound

HRID 894003Notes

Reaction equation

HRID 894003 reaction equation
[F:1][C:2]1[CH:22]=[CH:21][C:5]2[CH2:6][C:7](=[O:20])[C:8]3[CH:14]=[C:13]([CH:15]([CH3:19])[C:16](N)=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1.C(O)(=[O:25])C.Cl>O>[F:1][C:2]1[CH:22]=[CH:21][C:5]2[CH2:6][C:7](=[O:20])[C:8]3[CH:14]=[C:13]([CH:15]([CH3:19])[C:16]([OH:25])=[O:17])[CH:12]=[CH:11][C:9]=3[S:10][C:4]=2[CH:3]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 313Hydrochloric AcidHCID 12895873HCID 12895873, compound

Product 1

HCID 12895874HCID 12895874, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
100 °C

Procedure

To a mixture of 300 mg of 2-(10,11-dihydro-7-fluoro-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide and 3 ml of acetic acid was added 3 ml of hydrochloric acid, and the resulting mixture was stirred at 100° C. for 2 hours. After cooling, to this was added water, and the mixture was extracted with ethyl acetate. The extract was re-extracted with a dilute sodium hydroxide solution. 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 removed by distillation to obtain yellow crystals, which were recrystallized from benzene, thereby obtaining 200 mg (yield: 67%) of 2-(10,11-dihydro-7-fluoro-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as colorless crystals having a melting point of 147.5°-148° C.

Workup

  1. temperatureAfter cooling
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe extract was re-extracted with a dilute sodium hydroxide solution
  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. customThe solvent was removed by distillation
  8. customto obtain yellow crystals, which
  9. customwere recrystallized from benzene

Sources & evidence

ORD record
ord-e85ffc2cb4084357946b01c0326cde04
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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