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

HRID 276017Notes

Reaction equation

HRID 276017 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-d7d05d8a32b94460ba7ece517f580a53
Source dataset
uspto-grants-2002_03
Patent number
US06352985B1

Reaction notes

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