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Sulfuric Acid → N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

HRID 1846833
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1846833
C([O:8][C:9]1[C:10](=[O:26])[CH:11]=[C:12]([CH2:15][NH:16][S:17]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)(=[O:19])=[O:18])[O:13][CH:14]=1)C1C=CC=CC=1.S(=O)(=O)(O)O>C(O)(=O)C>[OH:8][C:9]1[C:10](=[O:26])[CH:11]=[C:12]([CH2:15][NH:16][S:17]([C:20]2[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=2)(=[O:19])=[O:18])[O:13][CH:14]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

4

Edukt 2

HCID 1118Sulfuric AcidHCID 86725690N-(5-benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide

Produkt 1

HCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamideAusbeute 85,7 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

N-(5-Benzyloxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (7-01) (2.0 g, 5.39 mmol) was dissolved in acetic acid (25.0 mL) and sulfuric acid (0.058 mL) was added, then the reaction mixture was heated up to 80° C. for 24 h. After completion of the reaction, the mixture was cooled to room temperature and concentrated under vacuum. It was then diluted with water and extracted with ethyl acetate. The combined organic layer was washed with water and brine, dried over Na2SO4 and concentrated under reduced pressure. It was then purified by washing with hexane to get N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide (8-01) (1.3 gm, 85.53%) as a brown solid.

Aufarbeitung

  1. customAfter completion of the reaction
  2. temperaturethe mixture was cooled to room temperature
  3. concentrationconcentrated under vacuum
  4. additionIt was then diluted with water
  5. extractionextracted with ethyl acetate
  6. washThe combined organic layer was washed with water and brine
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated under reduced pressure
  9. customIt was then purified
  10. washby washing with hexane

Quellen und Nachweise

ORD-Eintrag
ord-a9b93d1c1c6543eab570f72b4c247c45
Quelldatensatz
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08952039B2

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