Acetic Acid → HCID 12895870, compound

HRID 894001Notes

Reaction equation

HRID 894001 reaction equation
C[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.Br.C(O)(=[O:27])C>CCCCCC>[OH: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:19])=[O:27])=[CH:16][C:10]=3[C:9](=[O:22])[CH2:8][C:7]=2[CH:23]=1

Participants

5

Reactant 3

HCID 176Acetic AcidHCID 260Hydrogen BromideHCID 12895859HCID 12895859, compound

Product 1

HCID 12895870HCID 12895870, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 8058HexaneSolvent

Procedure

A mixture of 130 mg of 2-(10,11-dihydro-8-methoxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionamide, 20 ml of hydrobromic acid and 8 ml of acetic acid was refluxed with stirring for 3 hours. The solvent was distilled off to obtain a residue, which was extracted with chloroform. The extract was washed with a saturated sodium chloride solution and dried over anhydrous sodium sulfate. The solvent was distilled off to obtain crude crystals, which were recrystallized from ethyl acetate--n-hexane to obtain 102 mg (yield: 82%) of 2-(10,11-dihydro-8-hydroxy-11-oxodibenzo[b,f]thiepin-2-yl)-propionic acid as a light yellow powder having a melting point of 216°-217° C.

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off
  3. customto obtain a residue, which
  4. extractionwas extracted with chloroform
  5. washThe extract was washed with a saturated sodium chloride solution
  6. dry with materialdried over anhydrous sodium sulfate
  7. distillationThe solvent was distilled off
  8. customto obtain crude crystals, which
  9. customwere recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-78d73791b8534761857d35f4f5f6e426
Source dataset
uspto-grants-1981_08
Patent number
US04282245

Reaction notes

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