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

HRID 1846833Notes

Reaction equation

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

Participants

Conditions

Temperature: 80 °C

Procedure

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.

Workup

customAfter completion of the reaction
temperaturethe mixture was cooled to room temperature
concentrationconcentrated under vacuum
additionIt was then diluted with water
extractionextracted with ethyl acetate
washThe combined organic layer was washed with water and brine
dry with materialdried over Na2SO4
concentrationconcentrated under reduced pressure
customIt was then purified
washby washing with hexane

Sources & evidence

ORD record: ord-a9b93d1c1c6543eab570f72b4c247c45
Source dataset: uspto-grants-2015_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08952039B2

Reaction notes

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