Ammonia → 3-(4-Methoxy-benzoyl)-benzenesulfonamide

HRID 1810147Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1810147
[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:15](Cl)(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1.[NH3:21]>ClCCl.CO>[CH3:1][O:2][C:3]1[CH:20]=[CH:19][C:6]([C:7]([C:9]2[CH:10]=[C:11]([S:15]([NH2:21])(=[O:17])=[O:16])[CH:12]=[CH:13][CH:14]=2)=[O:8])=[CH:5][CH:4]=1

Komponenten

5

Edukt 2

HCID 222AmmoniaHCID 581074213-(4-Methoxy-benzoyl)-benzenesulfonyl chloride

Produkt 1

HCID 442352773-(4-Methoxy-benzoyl)-benzenesulfonamideAusbeute 50 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 887MethanolLösungsmittelHCID 6344DichloromethaneLösungsmittel

Versuchsvorschrift

3-(4-Methoxy-benzoyl)-benzenesulfonyl chloride is dissolved in dichloromethane (10 ml) and treated with 1.7 mL of a 2 M solution of ammonia in methanol. The reaction is stirred at ambient temperature for 2 hours and quenched with 1N HCl. The organic phase is separated and evaporated under reduced pressure to give the crude sulfonamide. Purification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%) yielded 100 mg (50% yield) of the title compound. 1H NMR (CDCl3, 300 MHz): 8.3 (t, 1H, J=1.6 Hz), 8.1 (m, 1H), 7.95 (m, 1H), 7.8 (d, 2H, J=6.98 Hz), 7.65 (t, 1H, J=7.8 Hz), 7.0 (d, 2H, J=6.98 Hz), 4.95 (s, 2H), 3.9 (s, 3H). MP: 119-122° C. LCMS Elution time 0.81 MS (m/z): 291 (M+1). CHN Calc C, 57.72; H, 4.50; N, 4.81 Found C, 57.65; H, 4.33; N, 4.69

Aufarbeitung

  1. customquenched with 1N HCl
  2. customThe organic phase is separated
  3. customevaporated under reduced pressure
  4. customto give the crude sulfonamide
  5. customPurification by silica gel chromatography (gradient of ethyl acetate in hexanes 5-25%)

Quellen und Nachweise

ORD-Eintrag
ord-f8dbce956b7f413a95409eec14a7b577
Quelldatensatz
uspto-grants-2013_01
Patentnummer
US08362063B2

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