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

HRID 1276883

Reaction equation

HRID 1276883 reaction equation
[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

Participants

5

Reactant 3

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

Product 1

HCID 18315416N-benzenesulfonyl-4-acetylamino-3-nitrobenzamideYield 78.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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)

Sources & evidence

ORD record
ord-ad51ec969bcd42e5aee59aaf2d89d0fc
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Linked notes

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