Sodium Hydroxide → 7-[4-(2-Propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid

HRID 1169508Notes

Reaction equation

HRID 1169508 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:31]=[CH:30][C:11]([O:12][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:10][CH:9]=1)[CH2:2][CH3:3].[OH-].[Na+]>C1COCC1.CO>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([O:12][C:13]2[CH:14]=[CH:15][C:16]3[S:22](=[O:24])(=[O:23])[CH2:21][CH2:20][C:19]([C:25]([OH:27])=[O:26])=[CH:18][C:17]=3[CH:29]=2)=[CH:30][CH:31]=1)[CH2:2][CH3:3]

Participants

5

Reactant 2

HCID 14798Sodium HydroxideHCID 22990012Methyl 7-[4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Product 1

HCID 229900427-[4-(2-Propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 64.5%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
65 °C

Procedure

To methyl 7-[4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate (0.40 g) dissolved in THF (12 ml)/methanol (6.0 ml) was added a 1 N aqueous solution (2.7 ml) of sodium hydroxide, and the resulting mixture was stirred at 65° C. for 16 hours. After cooling to the room temperature, the reaction mixture was concentrated under reduced pressure to remove a half of the solvent. A 1 N aqueous solution of sodium hydroxide (3.0 ml) was added to the resulting mixture, which was washed with ethyl acetate. After being adjusted to pH=about 5, the resulting aqueous layer was extracted with ethyl acetate and the extract was washed with an aqueous saturated solution of sodium chloride and was then dried with magnesium sulfate. After evaporation to remove the solvent, the resulting residue was washed with hexane/ethyl acetate (=8/1) to obtain 7-[4-(2-propoxyethoxy)phenoxy]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid (0.25 g).

Workup

  1. temperatureAfter cooling to the room temperature
  2. concentrationthe reaction mixture was concentrated under reduced pressure
  3. customto remove a half of the solvent
  4. additionA 1 N aqueous solution of sodium hydroxide (3.0 ml) was added to the resulting mixture, which
  5. washwas washed with ethyl acetate
  6. extractionthe resulting aqueous layer was extracted with ethyl acetate
  7. washthe extract was washed with an aqueous saturated solution of sodium chloride
  8. dry with materialwas then dried with magnesium sulfate
  9. customAfter evaporation
  10. customto remove the solvent
  11. washthe resulting residue was washed with hexane/ethyl acetate (=8/1)

Sources & evidence

ORD record
ord-1f6152a7c5eb47998b9bec9dd7ecd8d9
Source dataset
uspto-grants-2003_09
Patent number
US06627651B1

Reaction notes

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