Hydrochloric Acid → Methyl 7-bromo-5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-4-carboxylate

HRID 566075Notes

Reaction equation

[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH2:8][C:7](=[O:12])[C:6]=2[CH:13]=1.C[O-].[Na+].Cl.[C:18](=O)([O:21]C)[O:19][CH3:20]>>[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[S:11][CH2:10][CH2:9][CH:8]([C:18]([O:19][CH3:20])=[O:21])[C:7](=[O:12])[C:6]=2[CH:13]=1

Participants

Reactant 4

HCID 313Hydrochloric Acid

HCID 12021Dimethyl Carbonate

HCID 10942334Sodium Methoxide

HCID 177500407-Bromo-2,3,4,5-tetrahydro-1-benzothiepin-5-one

Product 1

HCID 18472488Methyl 7-bromo-5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-4-carboxylate

Procedure

To a solution of 7-bromo-2,3,4,5-tetrahydro-1-benzothiepin-5-one (13.5 g) in dimethyl carbonate (200 ml) was added at room temperature sodium methoxide (14.2 g), and the mixture was refluxed for 8 hours under nitrogen atmosphere. To the mixture was added 1N hydrochloric acid, and the mixture was extracted with ethyl acetate. The organic layer was washed with water and saturated brine, and dried with magnesium sulfate. Under reduced pressure, the solvent was evaporated to give brown prism of methyl 7-bromo-5-oxo-2,3,4,5-tetrahydro-1-benzothiepine-4-carboxylate (11.5 g).

Workup

temperaturethe mixture was refluxed for 8 hours under nitrogen atmosphere
extractionthe mixture was extracted with ethyl acetate
washThe organic layer was washed with water and saturated brine
dry with materialdried with magnesium sulfate
customUnder reduced pressure, the solvent was evaporated

Sources & evidence

ORD record: ord-464f50abf7d4402da71b9fb0a9acfd0f
Source dataset: uspto-grants-2001_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US06172061B2

Reaction notes

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