Sodium Hydroxide → 2-[4-(4-Methoxybutoxy)pyridine-2-yl]methylthio-1H-benzimidazole

HRID 727911Notes

Reaction equation

HRID 727911 reaction equation
[SH:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][CH2:23][O:24][CH3:25])[CH:16]=[CH:15][N:14]=1.[OH-].[Na+]>C(O)C>[CH3:25][O:24][CH2:23][CH2:22][CH2:21][CH2:20][O:19][C:17]1[CH:16]=[CH:15][N:14]=[C:13]([CH2:12][S:1][C:2]2[NH:6][C:5]3[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=3[N:3]=2)[CH:18]=1

Participants

5

Reactant 3

HCID 14798Sodium HydroxideHCID 151662232-Chloromethyl-4-(4-methoxybutoxy)pyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 151663272-[4-(4-Methoxybutoxy)pyridine-2-yl]methylthio-1H-benzimidazoleYield 70.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 2.55 g (0.017 mol) of 2-mercaptobenzimidazole, 5.09 g (0.022 mol) of 2-chloromethyl-4-(4-methoxybutoxy)pyridine, 0.84 g (0.020 mol) of 95% sodium hydroxide and 60 ml of ethanol was stirred at 40° C. for 1.5 hours. After the completion of the reaction, the reaction mixture was distilled to remove the solvent. The obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane) to obtain 4.13 g of the title compound.

Workup

  1. customAfter the completion of the reaction
  2. distillationthe reaction mixture was distilled
  3. customto remove the solvent
  4. customThe obtained residue was purified by silica gel column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-727e4dcd8a5642c897b6465dfdf72cd8
Source dataset
uspto-grants-1991_09
Patent number
US05045552

Reaction notes

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