Benzenesulfonamide → N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide

HRID 276023

Reaktionsgleichung

Reaktionsgleichung von HRID 276023
[C:1]([NH:4][C:5]1[CH:13]=[CH:12][C:8]([C:9]([OH:11])=O)=[CH:7][C:6]=1[N+:14]([O-:16])=[O:15])(=[O:3])[CH3:2].[C:17]1([S:23]([NH2:26])(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:17]1([S:23]([NH:26][C:9](=[O:11])[C:8]2[CH:12]=[CH:13][C:5]([NH:4][C:1](=[O:3])[CH3:2])=[C:6]([N+:14]([O-:16])=[O:15])[CH:7]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Komponenten

5

Edukt 3

HCID 7370BenzenesulfonamideHCID 737584-Acetamido-3-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Produkt 1

HCID 18315416N-benzenesulfonyl-4-acetylamino-3-nitrobenzamideAusbeute 78,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N′-carbonyldiimidazole (14.45 g) was added to a solution of 10.00 g of 4-acetylamino-3-nitrobenzoic acid in 300 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, 14.03 g of benzenesulfonamide and 13.58 g of diazabicycloundecene were added thereto, and the mixture was stirred at 100° C. for 72 hours. The reaction mixture was separated with the addition of chloroform and water. The organic layer was then concentrated, and 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 12.67 g of N-benzenesulfonyl-4-acetylamino-3-nitrobenzamide.

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 72 hours
  2. customThe reaction mixture was separated with the addition of chloroform and water
  3. concentrationThe organic layer was then concentrated
  4. customthe resulting residue was purified through silica-gel column chromatography (eluent
  5. additiona mixture of ethyl acetate and methanol at a ratio of 4:1)

Quellen und Nachweise

ORD-Eintrag
ord-5431c869c2e0400b9d0d9f80ddb4dede
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06352985B1

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