4-Chlorobenzenesulfonyl chloride → 1-(4-chlorobenzenesulfonyl)-5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole

HRID 411612Notes

Reaction equation

HRID 411612 reaction equation
[F:1][CH:2]([F:26])[O:3][C:4]1[CH:25]=[CH:24][C:7]2[NH:8][C:9]([S:11]([CH2:13][C:14]3[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=3)=[O:12])=[N:10][C:6]=2[CH:5]=1.[Na].C(=O)([O-])[O-].[Na+].[Na+].[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41](Cl)(=[O:43])=[O:42])=[CH:37][CH:36]=1>ClCCl>[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:8]2[C:7]3[CH:24]=[CH:25][C:4]([O:3][CH:2]([F:1])[F:26])=[CH:5][C:6]=3[N:10]=[C:9]2[S:11]([CH2:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=2)=[O:12])(=[O:43])=[O:42])=[CH:37][CH:36]=1.[Cl:34][C:35]1[CH:40]=[CH:39][C:38]([S:41]([N:10]2[C:6]3[CH:5]=[C:4]([O:3][CH:2]([F:1])[F:26])[CH:25]=[CH:24][C:7]=3[N:8]=[C:9]2[S:11]([CH2:13][C:14]2[C:19]([O:20][CH3:21])=[C:18]([O:22][CH3:23])[CH:17]=[CH:16][N:15]=2)=[O:12])(=[O:43])=[O:42])=[CH:37][CH:36]=1

Participants

7

Reactant 4

HCID 73984-Chlorobenzenesulfonyl chlorideHCID 10340Sodium CarbonateHCID 5360545SodiumHCID 178493215HCID 178493215, compound

Product 2

HCID 158952261-(4-chlorobenzenesulfonyl)-5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazoleHCID 185412221-(4-chlorobenzenesulfonyl)-6-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
4 °C

Procedure

5-Difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole, sodium salt sesquihydrate (432 mg, 1 mmole) was suspended in 30 ml of dichloromethane in the presence of anhydrous sodium carbonate (100 mg). 4-Chlorobenzenesulfonyl chloride (211 mg, 1 mmole) was added to the suspension and stirred at 4° C. overnight. The organic layer was separated by filtration and concentrated under reduced pressure. The residual solid was crystallized from dichloromethane-ethyl ether-heptane. 417 mg of isomer, 1-(4-chlorobenzenesulfonyl)-5-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole and 1-(4-chlorobenzenesulfonyl)-6-difluoromethoxy-2-[(3,4-dimethoxy-2-pyridyl)methylsulfinyl]-1H-benzimidazole (5:4 ratio by NMR), was obtained. Yield 74.5% M.P. 82-83° C.

Workup

  1. customThe organic layer was separated by filtration
  2. concentrationconcentrated under reduced pressure
  3. customThe residual solid was crystallized from dichloromethane-ethyl ether-heptane

Sources & evidence

ORD record
ord-e431d9d8b7744a37b059cd7d98da4326
Source dataset
uspto-grants-2003_05
Patent number
US06559167B1

Reaction notes

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