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

HRID 1978595Notes

Reaction equation

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

Participants

Conditions

Temperature: 70 °C

Procedure

To a solution of methyl 7-(4-isopropoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (250 mg) in 1,2-dimethoxyethane (10 ml) was added 6N hydrochloric acid (3 ml), and the mixture was stirred at 70° C. for 18 hours. To the mixture were added 1,2-dimethoxyethane (10 ml) and 6N hydrochloric acid (5 ml), and the mixture was stirred at 70° C. for 4 days, 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 hexane to give colorless crystals of 7-(4-isopropoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (230.3 mg).

Workup

stirringthe mixture was stirred at 70° C. for 4 days
temperaturecooled to room temperature
extractionextracted with ethyl acetate
washThe organic layer was washed with saturated brine
dry with materialdried with magnesium sulfate
concentrationconcentrated under reduced pressure
customto give crystals, which
filtrationwere collected by filtration
washThe crystals were washed with hexane

Sources & evidence

ORD record: ord-4b02a919e39540d08fd6e4de8a09e27f
Source dataset: uspto-grants-2001_05
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06235771B1

Reaction notes

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