Benzenesulfonamide → 6-Benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole

HRID 1276905Notes

Reaction equation

HRID 1276905 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.[C:22]1([S:28]([NH2:31])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:22]1([S:28]([NH:31][C:1]([C:4]2[CH:5]=[CH:6][C:7]3[N:11]=[C:10]([CH3:12])[N:9]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[Cl:20])[C:8]=3[CH:21]=2)=[O:3])(=[O:30])=[O:29])[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 186808176-Carboxy-1-(2-Chlorobenzyl)-2-MethylbenzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 179386716-Benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazoleYield 67.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N'-carbonyldiimidazole (5.41 g) was added at a time to a solution of 5.02 g of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole in 110 ml of N,N-dimethylformamide, and the mixture was stirred at room temperature for 1 hour. Subsequently, a solution of 5.24 g of benzenesulfonamide and 5.08 g of diazabicycloundecene in 20 ml of N,N-dimethylformamide was added thereto, and the mixed solution was stirred at 100° C. for 70 hours. The reaction solution was cooled, and the solvent was distilled off under reduced pressure. Water and chloroform were added to the residue, and 10% hydrochloric acid was added thereto while being stirred until the aqueous layer was acidified. The solution was extracted twice with chloroform. The organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate, and a part of the solvent was distilled off under reduced pressure. The crystals precipitated were separated through filtration, and were dried to give 4.96 g of 6-benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole (163).

Workup

  1. stirringthe mixed solution was stirred at 100° C. for 70 hours
  2. temperatureThe reaction solution was cooled
  3. distillationthe solvent was distilled off under reduced pressure
  4. additionWater and chloroform were added to the residue, and 10% hydrochloric acid
  5. additionwas added
  6. stirringwhile being stirred until the aqueous layer
  7. extractionThe solution was extracted twice with chloroform
  8. washThe organic layer was washed with a saturated aqueous solution of sodium hydrogencarbonate
  9. distillationa part of the solvent was distilled off under reduced pressure
  10. customThe crystals precipitated
  11. customwere separated through filtration
  12. customwere dried

Sources & evidence

ORD record
ord-9cb8f006421041a7b663b6f68aa2d5e4
Source dataset
uspto-grants-2000_12
Patent number
US06166219

Reaction notes

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