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

HRID 1699614Notes

Reaction equation

HRID 1699614 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 58.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

N,N′-carbonyldiimidazole (45.8 g) is added all at once to an N,N-dimethyl-formamide (950 ml) solution of 6-carboxy-1-(2-chlorobenzyl)-2-methylbenzimidazole (45.0 g) (example 75), and the solution is stirred for one hour at room temperature. Subsequently, benzenesulfonamide (47.1 g) and diazabicycloundecene (35.0 g) are added, and the solution is stirred for 70 hours at 100° C. The reaction solution is cooled and the solvent is removed through evaporation under reduced pressure. Water (300 ml) and methanol (200 ml) are added to the residue, and moreover, 35% hydrochloric acid is added to adjust the acidity of the solution to pH 5.5. Precipitated crystals are separated through filtration, washed with a mixture solution (200 ml) of methanol and water (1/1), dried and thus, 6-benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole (38.4 g) is obtained. In addition, water is added to filtrates and crystals precipitated. The crystals are separated through filtration, washed with water, dried and thus, of the material (13.3 g) is obtained. Both sets of crystals are gathered and dissolved by adding acetone (3300 ml) and water (900 ml) and by heating. The solvent is removed through evaporation as this solution is heated. Then the solution is cooled. Precipitated crystals are separated through filtration, dried, and thus, of 6-benzenesulfonylcarbamoyl-1-(2-chlorobenzyl)-2-methylbenzimidazole (33.8 g) is obtained. 1H-NMR (DMSO-d6δ): 2.53 (3H, s), 5.46 (2H, s), 6.34 (1H, d, J=7.8 Hz), 7.11 (1H, m), 7.27 (1H, m), 7.48 (1H, m), 7.52 (2H, m), 7.60 (1H, m), 7.69 (1H, d, J=8.6Hz), 7.90 (1H, m), 8.09 (2H, m), 8.11 (1H, s), 11.84 (1H, br s).

Workup

  1. stirringthe solution is stirred for 70 hours at 100° C
  2. temperatureThe reaction solution is cooled
  3. customthe solvent is removed through evaporation under reduced pressure
  4. additionWater (300 ml) and methanol (200 ml) are added to the residue
  5. addition35% hydrochloric acid is added
  6. customPrecipitated crystals
  7. customare separated through filtration
  8. washwashed with a mixture solution (200 ml) of methanol and water (1/1)
  9. customdried

Sources & evidence

ORD record
ord-8c75848207a04231b6ef18b5c6274c90
Source dataset
uspto-grants-2002_02
Patent number
US06348032B1

Reaction notes

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