Imidazole → HCID 178432232, compound

HRID 2099851Notes

Reaction equation

HRID 2099851 reaction equation
[CH3:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][C:9]([CH2:11][OH:12])=[CH:10][C:4]=2[N:3]=1.[Si:13](Cl)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14].N1C=CN=C1>CN(C=O)C>[Si:13]([O:12][CH2:11][C:9]1[CH:8]=[CH:7][C:5]2[NH:6][C:2]([CH3:1])=[N:3][C:4]=2[CH:10]=1)([C:16]([CH3:19])([CH3:18])[CH3:17])([CH3:15])[CH3:14]

Participants

5

Reactant 3

HCID 795ImidazoleHCID 28928tert-Butyldimethylsilyl chlorideHCID 178432216HCID 178432216, compound

Product 1

HCID 178432232HCID 178432232, compoundYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a DMF solution (10 mL) of (2-methyl-1H-benzimidazol-5-yl)methanol (811 mg) were added tert-butyldimethylsilyl chloride (904 mg) and imidazole (680 mg), followed by 2 hours of stirring at room temperature. The reaction solution was concentrated, water was added thereto, the mixture was extracted with chloroform, and the extract was dried over anhydrous magnesium sulfate. The organic layer was concentrated under reduced pressure and the obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v)) to obtain 5-(tert-butyldimethylsilyloxymethyl)-2-methyl-1H-benzimidazole (1305 mg, 94%).

Workup

  1. concentrationThe reaction solution was concentrated
  2. additionwater was added
  3. extractionthe mixture was extracted with chloroform
  4. dry with materialthe extract was dried over anhydrous magnesium sulfate
  5. concentrationThe organic layer was concentrated under reduced pressure
  6. customthe obtained residue was purified by silica gel column chromatography (eluent: chloroform:methanol=10:1 (v/v))

Sources & evidence

ORD record
ord-65f4ae6765e648b2b3a67eb4e66a91e6
Source dataset
uspto-grants-2009_08
Patent number
US07569688B2

Reaction notes

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