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

HRID 1978605Notes

Reaction equation

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

Participants

Conditions

Temperature: 100 °C

Procedure

In 1,2-dimethoxyethane (15.3 ml) was dissolved methyl 7-(4-methyl-2-thienyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate. (510 mg), and to the solution was added 6N hydrochloric acid (10.2 ml). The mixture was stirred at 100° C. for 15 hours and cooled to room temperature. Under reduced pressure, the solvent was evaporated. To the residue,were added ethyl acetate and potassium carbonate solution, and the mixture was extracted with water. To the solution was added 6N hydrochloric acid, and the solution was made pH 4-5, extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 7-(4-methyl-2-thienyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (459 mg).

Workup

temperaturecooled to room temperature
customUnder reduced pressure, the solvent was evaporated
additionTo the residue,were added ethyl acetate and potassium carbonate solution
extractionthe mixture was extracted with water
additionTo the solution was added 6N hydrochloric acid
extractionextracted with ethyl acetate
washwashed with saturated brine
dry with materialdried with magnesium sulfate
customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record: ord-b8f8600acfff448da21d8681cfb3191d
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235771B1

Reaction notes

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