Diethyl Sulfate → (1-Ethyl-1H-benzimidazol-2-yl)methanol

HRID 1884816Notes

Reaction equation

HRID 1884816 reaction equation
[OH:1][CH2:2][C:3]1[NH:4][C:5]2[CH:11]=[CH:10][CH:9]=[CH:8][C:6]=2[N:7]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:18](OS(OCC)(=O)=O)[CH3:19]>CO>[CH2:18]([N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[CH:11][C:5]=2[N:4]=[C:3]1[CH2:2][OH:1])[CH3:19]

Participants

5

Reactant 3

HCID 6163Diethyl SulfateHCID 11430Potassium CarbonateHCID 785692-(Hydroxymethyl)-1H-benzimidazole

Product 1

HCID 799599(1-Ethyl-1H-benzimidazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

99.2 mg (0.67 mmol) 2-hydroxymethylbenzimidazole was dissolved in 3 ml methanol. Potassium carbonate (103.1 g, 0.75 mmol) and diethylsulfate (442 μl 3.38 mmol) were added to the reaction mixture. Solution was stirred and refluxed overnight. The reaction mixture was then evaporated to dryness and purified on silica using gradient elution (chloroform to 5% methanol in chloroform) to obtain white crystals of 1-ethyl-2-hydroxymethylbenzimidazole, 41 mg (32%).

Workup

  1. temperaturerefluxed overnight
  2. customThe reaction mixture was then evaporated to dryness
  3. custompurified on silica using gradient elution (chloroform to 5% methanol in chloroform)

Sources & evidence

ORD record
ord-5fd2c8a905304dbaaeced6642ec7ae4b
Source dataset
uspto-grants-2004_07
Patent number
US06767909B2

Reaction notes

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