Sodium Hydroxide → 2-[4-(3-Methoxypropoxy)pyridine-2-yl]methylthio-1H-benzimidazole

HRID 357567Notes

Reaction equation

HRID 357567 reaction equation
[SH:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.Cl[CH2:12][C:13]1[CH:18]=[C:17]([O:19][CH2:20][CH2:21][CH2:22][O:23][CH3:24])[CH:16]=[CH:15][N:14]=1.[OH-].[Na+]>C(O)C>[CH3:24][O: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 151662252-Chloromethyl-4-(3-methoxypropoxy)pyridineHCID 178527775HCID 178527775, compound

Product 1

HCID 151663302-[4-(3-Methoxypropoxy)pyridine-2-yl]methylthio-1H-benzimidazoleYield 99.3%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

A mixture comprising 1.50 g (0.01 mol) of 2-mercapto-1H-benzimidazole, 3.20 g (0.015 mol) of 2-chloromethyl-4-(3-methoxypropoxy)pyridine, 0.51 g (0.012 mol) of 95% sodium hydroxide and 60 ml of ethanol was stirred at 40° C. for 0.5 hour and filtered. The filtrate was concentrated under a reduced pressure and purified by silica gel column chromatography (ethyl acetate/n-hexane) to obtain 3.27 g of the title compound as a colorless crystal.

Workup

  1. filtrationfiltered
  2. concentrationThe filtrate was concentrated under a reduced pressure
  3. custompurified by silica gel column chromatography (ethyl acetate/n-hexane)

Sources & evidence

ORD record
ord-78ea2921d3704c649cb7ee803a1e0d3d
Source dataset
uspto-grants-1998_11
Patent number
US05840910

Reaction notes

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