Pyridine → N-3-Quinolinylbenzenesulfonamide

HRID 394554Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 394554
[NH2:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.N1C=CC=CC=1.[C:18]1([S:24](Cl)(=[O:26])=[O:25])[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1>C(#N)C.C(OCC)(=O)C>[N:4]1[C:5]2[C:10](=[CH:9][CH:8]=[CH:7][CH:6]=2)[CH:11]=[C:2]([NH:1][S:24]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:26])=[O:25])[CH:3]=1

Komponenten

6

Edukt 3

HCID 1049PyridineHCID 7369Benzenesulfonyl chlorideHCID 113753-Aminoquinoline

Produkt 1

HCID 16654646N-3-Quinolinylbenzenesulfonamide

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6342AcetonitrileLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
0 °C

Versuchsvorschrift

To a solution of 3-aminoquinoline (7.2 g, 50 mmol) in acetonitrile (150 mL) was added pyridine (25 mL) and the resulting mixture was cooled to 0° C. A solution of benzenesulfonyl chloride (7 mL, 55 mmol) in acetonitrile (20 mL) was added dropwise over 30 minutes. The mixture was allowed to warm to rt and stirred for 18 hours. The mixture was diluted with ethyl acetate (100 mL) and washed successively with 1N HCl, brine and saturated CuSO4, dried (MgSO4), and concentrated in vacuo to afford an oil. Purification by flash silica gel column chromatography eluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid. MS; (M+H)+=285

Aufarbeitung

  1. temperatureto warm to rt
  2. washwashed successively with 1N HCl, brine and saturated CuSO4
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customto afford an oil
  6. customPurification by flash silica gel column chromatography
  7. washeluting with 30% ethyl acetate in hexanes afforded compound C (13. g g, 95%) as a white solid

Quellen und Nachweise

ORD-Eintrag
ord-be7dfc7e9e8c4e32b0ec01ae27d2bc73
Quelldatensatz
uspto-grants-2003_08
Patentnummer
US06602883B1

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