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

HRID 1846833
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HRID 1846833 반응식
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
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4

반응물 2

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

생성물 1

HCID 86725691N-(5-hydroxy-4-oxo-4H-pyran-2-ylmethyl)-benzene sulfonamide수율 85.7%

시약·촉매·용매 1

HCID 176Acetic Acid용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a9b93d1c1c6543eab570f72b4c247c45
출처 데이터셋
uspto-grants-2015_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08952039B2

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