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

HRID 1515418Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1515418
[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): δ 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-167b9e479f0f4ac1b1ee7da7abec57bb
Quelldatensatz
uspto-grants-2012_07
Patentnummer
US08222424B2

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