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

HRID 1978575Notes

Reaction equation

HRID 1978575 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([O:22]C)=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:4][CH:3]=1.Cl>COCCOC>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[CH:10][C:11]3[S:17](=[O:19])(=[O:18])[CH2:16][CH2:15][C:14]([C:20]([OH:22])=[O:21])=[CH:13][C:12]=3[CH:24]=2)=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 313Hydrochloric AcidHCID 21995794Methyl 7-(4-fluorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 219959777-(4-Fluorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 93%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of methyl 7-(4-fluorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.55 g) in 1,2-dimethoxyethane (20 ml) was added 6N hydrochloric acid (10 ml), and the mixture was refluxed for 29 hours, cooled to room temperature, extracted with ethyl acetate, 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 and hexane to give pale yellow crystals of 7-(4-fluorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (490.7 mg).

Workup

  1. temperaturethe mixture was refluxed for 29 hours
  2. extractionextracted with ethyl acetate, saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customto give crystals, which
  6. filtrationwere collected by filtration
  7. washThe crystals were washed with diisopropylether and hexane

Sources & evidence

ORD record
ord-a72f859861ce4cf4839c5697fe7d4612
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

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