Potassium Carbonate → 2-[(3,4-Dimethoxypyrid-2-yl)methylthio]benzimidazole

HRID 649215Notes

Reaction equation

HRID 649215 reaction equation
[K].[SH:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].Br[CH2:19][C:20]1[C:25]([O:26][CH3:27])=[C:24]([O:28][CH3:29])[CH:23]=[CH:22][N:21]=1>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:27][O:26][C:25]1[C:20]([CH2:19][S:2][C:3]2[NH:4][C:5]3[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=3[N:7]=2)=[N:21][CH:22]=[CH:23][C:24]=1[O:28][CH3:29]

Participants

7

Reactant 4

HCID 11430Potassium CarbonateHCID 5462222PotassiumHCID 201428022-Bromomethyl-3,4-dimethoxypyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 139829512-[(3,4-Dimethoxypyrid-2-yl)methylthio]benzimidazoleYield 70.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a mixture of potassium salt of 2-mercaptobenzimidazole (1.45 g), potassium carbonate (1.0 g) and dimethylformamide (10 ml) was added dropwise with stirring a solution of 2-bromomethyl-3,4-dimethoxypyridine (1.18 g) in dimethylformamide (2 ml), and the mixture was stirred at room temperature for 30 minutes, to which chloroform (100 ml) was added. The reaction mixture was washed with water, 1N-sodium hydroxide and water in this order, dried (with sodium sulfate) and evaporated. The residue was purified by column chromatography on silica gel (chloroform-methanol (50:1)), to give 2-[(3,4-dimethoxypyrid-2-yl)methylthio]benzimidazole (1.08 g) as a light yellow oil.

Workup

  1. additionwas added dropwise
  2. additionwas added
  3. washThe reaction mixture was washed with water, 1N-sodium hydroxide and water in this order
  4. dry with materialdried (with sodium sulfate)
  5. customevaporated
  6. customThe residue was purified by column chromatography on silica gel (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-3b07f775633c410b828f38f438522b4b
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

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