(4-Nitrophenyl)methanesulfonamide → 1-(4-Aminophenyl)methanesulfonamide

HRID 583910Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 583910
[N+:1]([C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:11])=[O:10])=[CH:6][CH:5]=1)([O-])=O.[H][H]>[Pd].CN(C)C=O>[NH2:1][C:4]1[CH:14]=[CH:13][C:7]([CH2:8][S:9]([NH2:12])(=[O:10])=[O:11])=[CH:6][CH:5]=1

Komponenten

5

Edukt 2

HCID 2755281(4-Nitrophenyl)methanesulfonamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 108214071-(4-Aminophenyl)methanesulfonamideAusbeute 97,3 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

To 10% palladium on charcoal catalyst (3 g, 50% wet with water) under a nitrogen atmosphere was added a solution of 4-nitro-benzylsulfonamide (17.53 g, 81.1 mmol). in dimethylformamide (175 ml). The atmosphere of nitrogen was replaced with hydrogen and the mixture stirred vigourously for 5 h. The atmosphere was replaced with nitrogen and the mixture filtered through celite. The solvent was removed in vacuo and the residue triturated with diethylether to give a dark brown solid (14.7 g). The solid was heated in acetonitrile (440 ml) and filtered whilst hot (to remove excess catalyst). The filtrate was allowed to cool and the precipitate filtered off and dried in vacuo to give the title compound as a beige solid (12.32 g, 82%). δH [2H6]—DMSO 4.05 (2H, s); 5.11 (2H, s); 6.53 (2H, d, 8.2 Hz); 6.63 (2H, s); 7.01(2H,d, 8.2 Hz).

Aufarbeitung

  1. filtrationthe mixture filtered through celite
  2. customThe solvent was removed in vacuo
  3. customthe residue triturated with diethylether

Quellen und Nachweise

ORD-Eintrag
ord-9bbd69963680421094a9a4471d347832
Quelldatensatz
uspto-grants-2005_08
Patentnummer
US06924297B2

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