Water → 2-(1-methoxyethyl)-1H-1,3-benzodiazole

HRID 2231246Notes

Reaction equation

HRID 2231246 reaction equation
[OH:1][CH:2]([C:4]1[NH:5][C:6]2[CH:12]=[CH:11][CH:10]=[CH:9][C:7]=2[N:8]=1)[CH3:3].[H-].[Na+].[CH3:15]I.O>CN(C)C=O>[CH3:15][O:1][CH:2]([C:4]1[NH:8][C:7]2[CH:9]=[CH:10][CH:11]=[CH:12][C:6]=2[N:5]=1)[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 2059221-(1H-1,3-benzodiazol-2-yl)ethan-1-ol

Product 1

HCID 450784722-(1-methoxyethyl)-1H-1,3-benzodiazoleYield 53.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4.05 g of 1-hydroxyethylbenzimidazole in 25 ml of dimethylformamide was added 1.2 g of 50% sodium hydride in oil, and the mixture stirred for 30 minutes. Methyl iodide (3.55 g) was added and the reaction mixture stirred at room temperature overnight. Water (200 ml) was added and the product extracted with ethyl acetate. The extracts were combined, dried and concentrated to an oil which was chromatographed on 130 g of silica gel using 5% methanol in chloroform as the eluent to give 2.36 g of brown oil.

Workup

  1. stirringthe reaction mixture stirred at room temperature overnight
  2. extractionthe product extracted with ethyl acetate
  3. customdried
  4. concentrationconcentrated to an oil which
  5. customwas chromatographed on 130 g of silica gel using 5% methanol in chloroform as the eluent

Sources & evidence

ORD record
ord-303ea52e2aa3477f87138105d0de21f7
Source dataset
uspto-grants-1988_11
Patent number
US04782050

Reaction notes

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