Hydrogen Bromide → 7-Hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1169300Notes

Reaction equation

HRID 1169300 reaction equation
C[O:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[CH2:11][CH2:10][C:9]([C:15]([O:17]C)=[O:16])=[CH:8][C:7]=2[CH:19]=1.Br>C(O)(=O)C>[OH:2][C:3]1[CH:4]=[CH:5][C:6]2[S:12](=[O:14])(=[O:13])[CH2:11][CH2:10][C:9]([C:15]([OH:17])=[O:16])=[CH:8][C:7]=2[CH:19]=1

Participants

4

Reactant 2

HCID 260Hydrogen BromideHCID 22990167Methyl 7-methoxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 229900217-Hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 82.9%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of methyl 7-methoxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (300 mg), 48% hydrobromic acid (3 ml) and acetic acid (3 ml) was heated at reflux for 4 hours. After concentration under reduced pressure, 48% hydrobromic acid (3 ml) and acetic acid (3 ml) were further added to the reaction mixture, which was heated at reflux for 8 hours. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to obtain 7-hydroxy-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (224 mg) as light yellow crystals.

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 4 hours
  3. concentrationAfter concentration under reduced pressure, 48% hydrobromic acid (3 ml) and acetic acid (3 ml)
  4. additionwere further added to the reaction mixture, which
  5. temperaturewas heated
  6. temperatureat reflux for 8 hours
  7. concentrationAfter concentration under reduced pressure
  8. filtrationthe precipitated crystals were collected by filtration
  9. washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record
ord-813649f0bd4d455fb8dab86a688e78af
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

Loading…