Benzenesulfonamide, 3-nitro- → Benzenesulfonamide, 3-amino-

HRID 361728

Reaktionsgleichung

Reaktionsgleichung von HRID 361728
[N+:1]([C:4]1[CH:5]=[C:6]([S:10]([NH2:13])(=[O:12])=[O:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O>CCO.[Pd]>[NH2:1][C:4]1[CH:5]=[C:6]([S:10]([NH2:13])(=[O:11])=[O:12])[CH:7]=[CH:8][CH:9]=1

Komponenten

4

Edukt 1

HCID 67138Benzenesulfonamide, 3-nitro-

Produkt 1

HCID 7377Benzenesulfonamide, 3-amino-Ausbeute 100,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 702EthanolLösungsmittel

Versuchsvorschrift

A solution of 1.5 g (7.42 mmol) of 3-nitrobenzenesulfonamide in 50 ml of EtOH containing 150 mg of 10% palladium on carbon was placed on a Parr hydrogenator under H2 for 1 h. The reaction was filtered through a pad of celite washing with EtOH, and the filtrate was concentrated in vacuo to give 1.28 g (100%) of 3-aminobenzenesulfonamide which was used immediately in the next reaction. The title compound was prepared as in example 21 from 3-aminobenzenesulfonamide using intermediate C. Recrystallization from MeOH/Et2O provided 1.46 g (67%) of title compound as an off-white solid: mp 240°-242° C.; 1H NMR (D2O, 300 MHz) δ 7.86 (d, 1 H, J=8.1 Hz), 7.75 (s, 1 H), 7.63 (t, 1 H, J=8.1 Hz), 7.51 (d, 1 H, J=8.1 Hz), 2.30 (s, 3 H).

Aufarbeitung

  1. filtrationThe reaction was filtered through a pad of celite
  2. washwashing with EtOH
  3. concentrationthe filtrate was concentrated in vacuo

Quellen und Nachweise

ORD-Eintrag
ord-fe4f2101ef084b0185c7e95b7efe8dfd
Quelldatensatz
uspto-grants-1999_02
Patentnummer
US05866612

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