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

HRID 276047
Notes
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Reaction equation

HRID 276047 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]
ParticipantsProcedureWorkupSources & evidenceReaction notes

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 6228
Dimethylformamide
Solvent
2×

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-042b19705b0240928c7c3cd9ee2ac19d
Source dataset
uspto-grants-2002_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06352985B1

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes