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

HRID 1978573Notes

Reaction equation

HRID 1978573 reaction equation
[Cl: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>[Cl: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 21995682Methyl 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 219958327-(4-Chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 88.1%

Reagents, catalysts & solvents 1

HCID 80711,2-DimethoxyethaneSolvent

Conditions

Temperature
70 °C

Procedure

To a solution of methyl 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.95 g) in 1,2-dimethoxyethane (50 ml) was added 6N hydrochloric acid (30 ml), and the mixture was stirred at 70° C. for 64 hours. The mixture was cooled to room temperature, extracted with ethylacetate, saturated brine, dried with magnesium sulfate and concentrated under reduced pressure. Precipitated crystals were collected by filtration, and the crystals was washed with diisopropylether and hexane to give pale yellow crystals of 7-(4-chlorophenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (804.9 mg).

Workup

  1. temperatureThe mixture was cooled to room temperature
  2. extractionextracted with ethylacetate, saturated brine
  3. dry with materialdried with magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customPrecipitated crystals
  6. filtrationwere collected by filtration
  7. washthe crystals was washed with diisopropylether and hexane

Sources & evidence

ORD record
ord-a34c818f9d2549df97c97301a6928e11
Source dataset
uspto-grants-2001_05
Patent number
US06235771B1

Reaction notes

Loading…