Potassium Bicarbonate → N-benzenesulfonyl-4-acetylamino-3-aminobenzamide

HRID 1276884

Reaktionsgleichung

Reaktionsgleichung von HRID 1276884
[C:1]1([S:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([N+:22]([O-])=O)[CH:13]=2)(=[O:9])=[O:8])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])O.[K+].[H][H]>CO.O.[Pd]>[C:1]1([S:7]([NH:10][C:11](=[O:25])[C:12]2[CH:17]=[CH:16][C:15]([NH:18][C:19](=[O:21])[CH3:20])=[C:14]([NH2:22])[CH:13]=2)(=[O:8])=[O:9])[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

7

Edukt 3

HCID 516893Potassium BicarbonateHCID 18315416N-benzenesulfonyl-4-acetylamino-3-nitrobenzamideHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 18680999N-benzenesulfonyl-4-acetylamino-3-aminobenzamideAusbeute 57,8 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 23938PalladiumKatalysatorHCID 887MethanolLösungsmittelHCID 962WaterLösungsmittel

Versuchsvorschrift

N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide (12.67 g) was dissolved in 200 ml of methanol and 30 ml of water, and 7.59 g of potassium hydrogencarbonate were further added thereto. The mixture was hydrogenated in a hydrogen atmosphere using 2.53 g of 5% palladium on carbon as catalyst at 40° C. for 24 hours. The solid material was separated through filtration, and the filtrate was concentrated. The resulting residue was purified through silica-gel column chromatography (eluent: a mixture of ethyl acetate and methanol at a ratio of 4:1) to give 6.72 g of N-benzenesulfonyl-4-acetylamino-3-aminobenzamide.

Aufarbeitung

  1. customat 40° C.
  2. customfor 24 hours
  3. customThe solid material was separated through filtration
  4. concentrationthe filtrate was concentrated
  5. customThe resulting residue was purified through silica-gel column chromatography (eluent
  6. additiona mixture of ethyl acetate and methanol at a ratio of 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-548c83572ea743bcbf3a231aa47f2ab5
Quelldatensatz
uspto-grants-2000_12
Patentnummer
US06166219

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