Hydrochloric Acid → HCID 22990053, compound

HRID 1169469Notes

Reaction equation

[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:18](=[O:20])(=[O:19])[CH2:17][CH2:16][C:15]([C:21]([O:23]C)=[O:22])=[CH:14][C:13]=2[CH:25]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl>C1COCC1.CO>[CH2:1]([O:4][C:5]1[CH:6]=[C:7]([CH:26]=[CH:27][CH:28]=1)[O:8][C:9]1[CH:10]=[CH:11][C:12]2[S:18](=[O:19])(=[O:20])[CH2:17][CH2:16][C:15]([C:21]([OH:23])=[O:22])=[CH:14][C:13]=2[CH:25]=1)[CH2:2][CH3:3]

Participants

Conditions

Temperature: 65 °C

Procedure

Into a solution of methyl 7-(3-propoxyphenoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.53 g) in THF-methanol (10-5 ml) was added at room temperature a 1 M aqueous solution of potassium carbonate (2.6 ml), and the resulting mixture was stirred at 65° C. for 40 hours. After cooling to room temperature, 1 N hydrochloric acid (10 ml) was added to the reaction mixture, which was extracted with ethyl acetate. The organic layer was washed with an aqueous saturated solution of sodium chloride and was dried with magnesium sulfate. After concentration under reduced pressure, the precipitated crystals were collected by filtration. The crystals were washed with diisopropyl ether to obtain 7-(3-propoxyphenoxy)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (412 mg) as light yellow crystals.

Workup

temperatureAfter cooling to room temperature
extractionwas extracted with ethyl acetate
washThe organic layer was washed with an aqueous saturated solution of sodium chloride
dry with materialwas dried with magnesium sulfate
concentrationAfter concentration under reduced pressure
filtrationthe precipitated crystals were collected by filtration
washThe crystals were washed with diisopropyl ether

Sources & evidence

ORD record: ord-8976b60ff1f746f992923426040b7fa2
Source dataset: uspto-grants-2003_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06627651B1

Reaction notes

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