Potassium → 2-[(3-Methoxy-4-propoxypyrid-2-yl)methylthio]benzimidazole

HRID 649216Notes

Reaction equation

HRID 649216 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.Br[CH2:13][C:14]1[C:19]([O:20][CH3:21])=[C:18]([O:22][CH2:23][CH2:24][CH3:25])[CH:17]=[CH:16][N:15]=1>CN(C)C=O.C(Cl)(Cl)Cl>[CH3:21][O:20][C:19]1[C:14]([CH2:13][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:15][CH:16]=[CH:17][C:18]=1[O:22][CH2:23][CH2:24][CH3:25]

Participants

6

Reactant 3

HCID 5462222PotassiumHCID 139829492-Bromomethyl-3-methoxy-4-propoxypyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 139829502-[(3-Methoxy-4-propoxypyrid-2-yl)methylthio]benzimidazoleYield 69.1%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6228DimethylformamideSolvent2×

Procedure

To a solution of potassium salt of 2-mercaptobenzimidazole (0.4 g) in dimethylformamide (5 ml), was added dropwise a solution of 2-bromomethyl-3-methoxy-4-propoxypyridine (0.4 g) in dimethylformamide, and stirred at room temperature for 1 hour. The reaction mixture was diluted with chloroform (50 ml), washed with water, dried, and evaporated. The residue was purified by column chromatography on silica gel (chloroform-methanol (50:1)) to give 2-[(3-methoxy-4-propoxypyrid-2-yl)methylthio]benzimidazole (0.35 g) as a light brown oil.

Workup

  1. washwashed with water
  2. customdried
  3. customevaporated
  4. customThe residue was purified by column chromatography on silica gel (chloroform-methanol (50:1))

Sources & evidence

ORD record
ord-8541480066b84be0864b9bde5d975bf8
Source dataset
uspto-grants-1988_04
Patent number
US04738975

Reaction notes

Loading…