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

HRID 413597Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 413597
[CH2:1]([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]CC)=[O:24])=[CH:16][C:15]=3[CH:28]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3].O.C(=O)([O-])[O-].[K+].[K+].Cl>O1CCCC1.C(O)CO>[CH2:1]([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:28]=2)=[CH:7][CH:6]=1)[CH2:2][CH3:3]

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 962WaterHCID 11430Potassium CarbonateHCID 11773971Ethyl 7-(4-propoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylate

Produkt 1

HCID 111646457-(4-Propoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acidAusbeute 92,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 21863614Tetrahydrofuran ethylene glycolLösungsmittel

Reaktionsbedingungen

Temperatur
25 °C

Versuchsvorschrift

Ethyl 7-(4-propoxyphenyl)-1,1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxlate (1.0 g, 2.497 mmol) was dissolved in 15 ml of a mixed solution of tetrahydrofuran/ethylene glycol =2/1. Crystals were formed by adding 8.5 ml of water. Potassium carbonate (690 mg, 4.994 mmol) was added and the mixture was heated under reflux for 3.25 hours. Under reflux, 3.5 ml of a 3N hydrochloric acid was dropped to form crystals. After cooling, the mixture was stirred at 20-30° C. for 45minutes and for 1 hour while cooling in ice. After filtration, the residue was washed with 10 ml of a mixed solution of tetrahydrofuran/methanol/water=1/1/3. After vacuum drying (40° C.), 858 mg (Yield 92%) of 7-(4-propoxyphenyl)-1, 1-dioxo-2,3-dihydro-1-benzothiepine-4-carboxylic acid was obtained as pale yellowish white crystals.

Aufarbeitung

  1. customCrystals were formed
  2. temperaturethe mixture was heated
  3. temperatureunder reflux for 3.25 hours
  4. temperatureUnder reflux
  5. customto form crystals
  6. temperatureAfter cooling
  7. temperaturewhile cooling in ice
  8. filtrationAfter filtration
  9. washthe residue was washed with 10 ml of a mixed solution of tetrahydrofuran/methanol/water=1/1/3
  10. customAfter vacuum drying (40° C.)

Quellen und Nachweise

ORD-Eintrag
ord-734758dc8dac423ea35490c4b7def93e
Quelldatensatz
uspto-grants-2003_05
Patentnummer
US06566535B1

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