4-Nitrobenzenesulfonamide → 1-(2-Chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazole

HRID 1276908

Reaction equation

HRID 1276908 reaction equation
[C:1]([C:4]1[CH:5]=[CH:6][C:7]2[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=3[Cl:20])[C:8]=2[CH:21]=1)([OH:3])=O.[N+:22]([C:25]1[CH:30]=[CH:29][C:28]([S:31]([NH2:34])(=[O:33])=[O:32])=[CH:27][CH:26]=1)([O-:24])=[O:23].C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[Cl:20][C:15]1[CH:16]=[CH:17][CH:18]=[CH:19][C:14]=1[CH2:13][N:9]1[C:8]2[CH:21]=[C:4]([C:1](=[O:3])[NH:34][S:31]([C:28]3[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:30][CH:29]=3)(=[O:33])=[O:32])[CH:5]=[CH:6][C:7]=2[N:11]=[C:10]1[CH3:12]

Participants

5

Reactant 3

HCID 227844-NitrobenzenesulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 186810031-(2-Chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazoleYield 46.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N'-carbodiimidazole (0.432 g) was added at a time to a solution of 0.400 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole in 15 ml of N,N-dimethylformamide, and the solution was stirred at room temperature for 1 hour. Subsequently, a solution of 0.538 g of 4-nitrobenzenesulfonamide and 0.405 g of diazabicycloundecene in 5 ml of N,N-dimethylformamide, and the mixture was stirred at 100° C. for 84 hours. The reaction solution was cooled, and the solvent was distilled off under reduced pressure. Chloroform and hydrochloric acid were added to the residue, and the mixture was stirred to precipitate the crystals. The crystals precipitated were separated through filtration, and were dried to give 0.300 g of 1-(2-chlorobenzyl)-2-methyl-6-(4-nitrobenzenesulfonylcarbamoyl)benzimidazole (220).

Workup

  1. temperatureThe reaction solution was cooled
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionChloroform and hydrochloric acid were added to the residue
  4. stirringthe mixture was stirred
  5. customto precipitate the crystals
  6. customThe crystals precipitated
  7. customwere separated through filtration
  8. customwere dried

Sources & evidence

ORD record
ord-86bedd3ec8fe4d2b909a2f1c6b7011a6
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Linked notes

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