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

HRID 321972Notes

Reaction equation

HRID 321972 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-nitrobenzamideYield 50.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-carbonyldiimidazole (28.9 g) is added to an N,N-dimethylformamide (300 ml) solution of 3-acetylamino-4-nitro-benzoic acid (20.0 g), and the solution is stirred for 1 hour at room temperature. Further, benzenesulfonamide (28.0 g) and diazabicycloundecene (27.16 g) are added to the solution and the solution is stirred for 4 days at 100° C. The solvent is removed through evaporation under reduced pressure. Chloroform and 10% sodium hydroxide aqueous solution are added to the residue, and the mixture is stirred briskly. 10% hydrochloric acid is added to the aqueous layer until neutral. Chloroform is added and the solution is stirred briskly. The precipitated crystals are separated through filtration, and are dried. Thus, N-benzenesulfonyl-3-amino-4-nitrobenzamide (14.4 g) is obtained.

Workup

  1. stirringthe solution is stirred for 4 days at 100° C
  2. customThe solvent is removed through evaporation under reduced pressure
  3. additionChloroform and 10% sodium hydroxide aqueous solution are added to the residue
  4. stirringthe mixture is stirred briskly
  5. addition10% hydrochloric acid is added to the aqueous layer until neutral
  6. additionChloroform is added
  7. stirringthe solution is stirred briskly
  8. customThe precipitated crystals are separated through filtration
  9. customare dried

Sources & evidence

ORD record
ord-6718aa49e1c54bb0b543d12d6dbefcd3
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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