Water → 2-(methoxymethyl)-1H-benzimidazole

HRID 452189Notes

Reaction equation

HRID 452189 reaction equation
Cl[CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.[CH3:12][OH:13].C[O-].[Na+].O>CO>[CH3:12][O:13][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 785712-ChloromethylbenzimidazoleHCID 23694274Sodium methanolate methanol

Product 1

HCID 2429502-(methoxymethyl)-1H-benzimidazoleYield 19%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

2-Chloromethylbenzimidazole (1.67 g, 10 mmol) was suspended in methanol (34 mL), 28% sodium methoxide methanol solution (9.6 mL, 50 mmol) and water (50 mL) were added, and the mixture was stirred at room temperature for 20 min. The precipitated solid was collected by filtration, and purified by silica gel column chromatography (chloroform/methanol=100/0 to 93/7) to give the title compound (303 mg, 19%).

Workup

  1. filtrationThe precipitated solid was collected by filtration
  2. custompurified by silica gel column chromatography (chloroform/methanol=100/0 to 93/7)

Sources & evidence

ORD record
ord-531e5954d5dc4528ad35a8dfe02b238b
Source dataset
uspto-grants-2013_07
Patent number
US08486980B2

Reaction notes

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