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

HRID 413603
Notes
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Reaction equation

HRID 413603 reaction equation
[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:13]=[CH:12][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[S:23](=[O:25])(=[O:24])[CH2:22][CH2:21][C:20]([C:26]([O:28]CC)=[O:27])=[CH:19][C:18]=3[CH:31]=2)=[CH:10][CH:9]=1)[CH2:2][CH3:3].O.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.CO>[CH2:1]([O:4][CH2:5][CH2:6][O:7][C:8]1[CH:9]=[CH:10][C:11]([C:14]2[CH:15]=[CH:16][C:17]3[S:23](=[O:24])(=[O:25])[CH2:22][CH2:21][C:20]([C:26]([OH:28])=[O:27])=[CH:19][C:18]=3[CH:31]=2)=[CH:12][CH:13]=1)[CH2:2][CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 962Water2×HCID 11430Potassium CarbonateHCID 70033921Ethyl 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxlate

Product 1

HCID 219958267-[4-(2-Propoxyethoxy)phenyl]-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidYield 91.2%

Reagents, catalysts & solvents

2
HCID 887MethanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

Ethyl 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxlate (11 g, 24.7447 mmol) was dissolved in 110 ml of tetrahydrofuran and 55 ml of methanol, and then 93.5 ml of water was added. After adding potassium carbonate (6.84 g, 49.49 mmol), the mixture was heated under reflux for 4.5 hours. Under reflux, 39.6 ml of a 3N hydrochloric acid and 40 ml of water were dropped. After cooling, the mixture was stirred for 1 hour while cooling in ice. After filtration, the residue was washed with 88 ml of water. After vacuum drying (40° C.), 9.4 g (Yield 91.2%) of 7-(4-propoxyethoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid was obtained as pale yellowish white crystals.

Workup

  1. temperaturethe mixture was heated
  2. temperatureunder reflux for 4.5 hours
  3. temperatureUnder reflux
  4. temperatureAfter cooling
  5. temperaturewhile cooling in ice
  6. filtrationAfter filtration
  7. washthe residue was washed with 88 ml of water
  8. customAfter vacuum drying (40° C.)

Sources & evidence

ORD record
ord-1d5c1dc62ec148eead03e25b0f4511cd
Source dataset
uspto-grants-2003_05
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06566535B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes