4-Toluenesulfonyl chloride → HCID 67219535, compound

HRID 1258467Notes

Reaction equation

HRID 1258467 reaction equation
[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[NH:14][C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[H-].[Na+].[CH3:22][C:23]1[CH:28]=[CH:27][C:26]([S:29](Cl)(=[O:31])=[O:30])=[CH:25][CH:24]=1>CN(C)C=O>[CH2:1]([O:8][C:9]1[C:17]2[N:16]=[C:15]([CH3:18])[N:14]([S:29]([C:26]3[CH:27]=[CH:28][C:23]([CH3:22])=[CH:24][CH:25]=3)(=[O:31])=[O:30])[C:13]=2[CH:12]=[C:11]([Br:19])[CH:10]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 73974-Toluenesulfonyl chlorideHCID 24758Sodium hydrideHCID 672202147-(benzyloxy)-5-bromo-2-methyl-1H-benzo[d]imidazole

Product 1

HCID 67219535HCID 67219535, compoundYield 98.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 4-(benzyloxy)-6-bromo-2-methyl-1H-benzimidazole (79.2 g, 250 mmol, Step 1) in N,N-dimethylformamide (500 mL) was added sodium hydride (60% in mineral oil, 12.0 g, 300 mmol) at 0° C. After stirring at room temperature for 20 minutes, the reaction mixture was cooled to 0° C. To the mixture was added 4-methylbenzenesulfonyl chloride (47.6 g, 250 mmol) at 0° C., and the reaction mixture was stirred at room temperature for 30 minutes. The mixture was quenched with water, and the white precipitates were collected by filtration, washed with diisopropyl ether, and dried in vacuo at 70° C. for 7 hours to afford the title compound as a white solid (116 g, 98%).

Workup

  1. temperaturethe reaction mixture was cooled to 0° C
  2. stirringthe reaction mixture was stirred at room temperature for 30 minutes
  3. customThe mixture was quenched with water
  4. customthe white precipitates
  5. filtrationwere collected by filtration
  6. washwashed with diisopropyl ether
  7. customdried in vacuo at 70° C. for 7 hours

Sources & evidence

ORD record
ord-b7ab20a1accf40bebcb60e6062da4b26
Source dataset
uspto-grants-2013_06
Patent number
US08466166B2

Reaction notes

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