Hydrochloric Acid → 7-[4-(2-Ethoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1978688Notes

Reaction equation

[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:12]=[CH:11][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([O:27]C)=[O:26])=[CH:18][C:17]=3[CH:29]=2)=[CH:9][CH:8]=1)[CH3:2].Cl>COCCOC>[CH2:1]([O:3][CH2:4][CH2:5][O:6][C:7]1[CH:8]=[CH:9][C:10]([C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:23])(=[O:24])[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=3[CH:29]=2)=[CH:11][CH:12]=1)[CH3:2]

Participants

Conditions

Temperature: 100 °C

Procedure

To methyl 7-[4-(2-ethoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (4.35 g) were added 1,2-dimethoxyethane (87 ml) and 6N hydrochloric acid (43.5 ml), and the mixture was refluxed at 100° C. for 16 hours and cooled to room temperature. The mixture was extracted with ethyl acetate, washed with saturated brine and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give 7-[4-(2-ethoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (3.7 g).

Workup

temperaturecooled to room temperature
extractionThe mixture was extracted 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-37781d8661934a53817e34a7a3a46fc5
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235771B1

Reaction notes

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