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

HRID 276017
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 276017
C([NH:4][C:5]1[CH:6]=[C:7]([CH:11]=[CH:12][C:13]=1[N+:14]([O-:16])=[O:15])[C:8]([OH:10])=O)(=O)C.[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:8](=[O:10])[C:7]2[CH:11]=[CH:12][C:13]([N+:14]([O-:16])=[O:15])=[C:5]([NH2:4])[CH:6]=2)(=[O:25])=[O:24])[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 3

HCID 7370BenzenesulfonamideHCID 39330783-Acetamido-4-nitrobenzoic acidHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Produkt 1

HCID 18315560N-benzenesulfonyl-3-amino-4-nitrobenzamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

N,N′-carbonyldiimidazole (28.9 g) was added to a solution of 20.0 g of 3-acetylamino-4-nitrobenzoic acid in 300 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Further, 28.00 g of benzenesulfonamide and 27.16 g of diazabicycloundecene were added thereto, and the mixture was stirred at 100° C. for 4 days. The solvent was distilled off under reduced pressure. Chloroform and a 10% sodium hydroxide aqueous solution were added to the residue, and the mixture was vigorously stirred. The aqueous layer was neutralized with 10% hydrochloric acid, and the mixture was vigorously stirred with the addition of chloroform. The crystals precipitated were separated through filtration, and were dried to 14.4 g of N-benzenesulfonyl-3-amino-4-nitrobenzamide.

Aufarbeitung

  1. stirringthe mixture was stirred at 100° C. for 4 days
  2. distillationThe solvent was distilled off under reduced pressure
  3. additionChloroform and a 10% sodium hydroxide aqueous solution were added to the residue
  4. stirringthe mixture was vigorously stirred
  5. stirringthe mixture was vigorously stirred with the addition of chloroform
  6. customThe crystals precipitated
  7. customwere separated through filtration
  8. dry with materialwere dried to 14.4 g of N-benzenesulfonyl-3-amino-4-nitrobenzamide

Quellen und Nachweise

ORD-Eintrag
ord-d7d05d8a32b94460ba7ece517f580a53
Quelldatensatz
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06352985B1

Notizen zur Reaktion

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