Hydrochloric Acid → 7-(4-Butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1978599Notes

Reaction equation

HRID 1978599 reaction equation
[CH2:1]([O:5][C:6]1[CH:11]=[CH:10][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:23])(=[O:22])[CH2:20][CH2:19][C:18]([C:24]([O:26]C)=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:8][CH:7]=1)[CH2:2][CH2:3][CH3:4].Cl>COCCOC>[CH2:1]([O:5][C:6]1[CH:7]=[CH:8][C:9]([C:12]2[CH:13]=[CH:14][C:15]3[S:21](=[O:22])(=[O:23])[CH2:20][CH2:19][C:18]([C:24]([OH:26])=[O:25])=[CH:17][C:16]=3[CH:28]=2)=[CH:10][CH:11]=1)[CH2:2][CH2:3][CH3:4]

Participants

4

Reactant 2

HCID 313Hydrochloric Acid2×HCID 21995746Methyl 7-(4-butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 219956637-(4-Butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 80.6%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent2×

Procedure

To a solution of methyl 7-(4-butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (500 mg) in 1,2-dimethoxyethane (1Oml) was added 6N hydrochloric acid (5 ml), and the mixture was refluxed for 16 hours. To the mixture were added 1,2-dimethoxyethane (5 ml) and 6N hydrochloric acid (2 ml), and the mixture was refluxed for 4 hours, cooled to room temperature and extracted with ethyl acetate. The organic layer was washed with saturated brine, dried with magnesium sulfate and concentrated under reduced pressure to give crystals, which were collected by filtration. The crystals were washed with diisopropylether to give colorless crystals of 7-(4-butoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (388.9 mg).

Workup

  1. temperaturethe mixture was refluxed for 16 hours
  2. temperaturethe mixture was refluxed for 4 hours
  3. extractionextracted with ethyl acetate
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried with magnesium sulfate
  6. concentrationconcentrated under reduced pressure
  7. customto give crystals, which
  8. filtrationwere collected by filtration
  9. washThe crystals were washed with diisopropylether

Sources & evidence

ORD record
ord-4c08cab4900a4e23a6c5828e7b29c03c
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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