Benzenesulfonamide → 5-Benzenesulfonylcarbamoyl-2-benzyl-1-(2-chlorobenzyl)benzimidazole

HRID 321971Notes

Reaction equation

HRID 321971 reaction equation
[CH2:1]([C:8]1[N:12]([CH2:13][C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=2[Cl:20])[C:11]2[CH:21]=[CH:22][C:23]([C:25](O)=[O:26])=[CH:24][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:28]1([S:34]([NH2:37])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1.C1(C2CCCCCCCCCC=2)CCCCCCCCNN=1>CN(C)C=O>[C:28]1([S:34]([NH:37][C:25]([C:23]2[CH:22]=[CH:21][C:11]3[N:12]([CH2:13][C:14]4[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=4[Cl:20])[C:8]([CH2:1][C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=4)=[N:9][C:10]=3[CH:24]=2)=[O:26])(=[O:36])=[O:35])[CH:33]=[CH:32][CH:31]=[CH:30][CH:29]=1

Participants

5

Reactant 3

HCID 7370BenzenesulfonamideHCID 186810562-Benzyl-5-carboxy-1-(2-chlorobenzyl) benzimidazoleHCID 536302743-(Cycloundecen-1-yl)-1,2-diazacycloundec-2-ene

Product 1

HCID 98278875-Benzenesulfonylcarbamoyl-2-benzyl-1-(2-chlorobenzyl)benzimidazoleYield 70.1%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

N,N′-carbonyldiimidazole (0.401 g) is added all at once to an N,N-dimethylformamide (20 ml) solution of 2-benzyl-5-carboxy-1-(2-chlorobenzyl) benzimidazole (0.466 g), and the solution is stirred for one hour at room temperature. Subsequently, a N,N-dimethylformamide (5 ml) solution of benzenesulfonamide (0.389 g) and diazabicycloundecene (0.377 g) is added, and the solution is stirred for 48 hours at 100° C. The reaction solution is cooled, and the solvent is removed through evaporation under reduced pressure. This material is dissolved in a mixture solution of methanol and water. The pH is adjusted to pH 5˜6 using 10% hydrochloric acid. Precipitated crystals are separated through filtration, and are dried. Thus, 5-benzenesulfonylcarbamoyl-2-benzyl-1-(2-chlorobenzyl)benzimidazole (0.447 g) is obtained.

Workup

  1. stirringthe solution is stirred for 48 hours at 100° C
  2. temperatureThe reaction solution is cooled
  3. customthe solvent is removed through evaporation under reduced pressure
  4. dissolutionThis material is dissolved in a mixture solution of methanol and water
  5. customPrecipitated crystals
  6. customare separated through filtration
  7. customare dried

Sources & evidence

ORD record
ord-39f4988d685d46ebb28951e8b58776a3
Source dataset
uspto-grants-2001_04
Patent number
US06211177B1

Reaction notes

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