Benzenesulfonyl chloride → N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

HRID 492082

Reaktionsgleichung

Reaktionsgleichung von HRID 492082
[NH2:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[C:8](=[O:12])[CH2:7][CH2:6][CH2:5]2.[C:13]1([S:19](Cl)(=[O:21])=[O:20])[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>N1C=CC=CC=1.O>[O:12]=[C:8]1[CH2:7][CH2:6][CH2:5][C:4]2[CH:3]=[C:2]([NH:1][S:19]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)(=[O:21])=[O:20])[CH:11]=[CH:10][C:9]1=2

Komponenten

5

Edukt 2

HCID 7369Benzenesulfonyl chlorideHCID 3395376-Amino-1,2,3,4-tetrahydronaphthalen-1-one

Produkt 1

HCID 68830588N-(5-oxo-5,6,7,8-tetrahydronaphthalen-2-yl)benzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittelHCID 1049PyridineLösungsmittel

Reaktionsbedingungen

Temperatur
23 °C

Versuchsvorschrift

To a solution of 0.46 gram (2.85 mmole) 6-amino-3,4-dihydro-2H-naphthalen-1-one in 25 mL pyridine was added 0.605 grams (3.42 mmoles) benzenesulfonyl chloride. The reaction mixture was stirred at 23° C. for 24 hours. The mixture was diluted with 100 mL water and extracted with 200 mL ethyl acetate. The organic phase was dried (magnesium sulfate) and concentrated under reduced pressure. The residue was subjected to low pressure column chromatography over silica gel 230-400 mesh eluting with 50% ethyl acetate in hexane. The title compound was obtained as a solid, 0.48 gram (56%), m.p. 164-165° C., M−H=300.

Aufarbeitung

  1. extractionextracted with 200 mL ethyl acetate
  2. dry with materialThe organic phase was dried (magnesium sulfate)
  3. concentrationconcentrated under reduced pressure
  4. washeluting with 50% ethyl acetate in hexane

Quellen und Nachweise

ORD-Eintrag
ord-f9260c5fe5154020ab983ebb14106707
Quelldatensatz
uspto-grants-2009_05
Patentnummer
US07531577B2

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