1H-Benzimidazole, 1-methyl- → (1-methyl-1H-1,3-benzodiazol-2-yl)methanol

HRID 1016416Notes

Reaction equation

HRID 1016416 reaction equation
[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[CH:3]1.[C:11](=O)([O-])[OH:12].[Na+]>C=O>[CH3:1][N:2]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]=[C:3]1[CH2:11][OH:12]

Participants

4

Reactant 2

HCID 958901H-Benzimidazole, 1-methyl-HCID 516892Sodium Bicarbonate

Product 1

HCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanol

Reagents, catalysts & solvents 1

HCID 712FormaldehydeSolvent

Procedure

1-Methylbenzimidazole (5.0 g, 0.038 mol) was stirred at reflux in 37 wt % aqueous formaldehyde (50 ml) for 24 h. The solution was allowed to cool to room temperature then basified with saturated sodium hydrogen carbonate solution and then extracted with. dichloromethane (3×50 ml). The combined organic layers were dried over magnesium sulfate and were concentrated in vacuo. The residue was purified by flash chromatography on silica gel, eluting with 2.5 to 10% methanol in dichloromethane. The resultant semi-solid was triturated with isohexane to yield a solid, which was then recrystallised from ethyl acetate/isohexane, yielding (1-methyl-1H-benzimidazol-2-yl)methanol as a white solid (0.71 g). Data for the title compound: 1H NMR (400 MHz, CDCl3) δ 3.81 (3H, s), 4.89 (2H, s), 7.26 (3H, m), 7.69 (1H, m); MS (ES+) m/e 163 [MH]+.

Workup

  1. extractionextracted with
  2. dry with materialThe combined organic layers were dried over magnesium sulfate
  3. concentrationwere concentrated in vacuo
  4. customThe residue was purified by flash chromatography on silica gel
  5. washeluting with 2.5 to 10% methanol in dichloromethane
  6. customThe resultant semi-solid was triturated with isohexane
  7. customto yield a solid, which
  8. customwas then recrystallised from ethyl acetate/isohexane

Sources & evidence

ORD record
ord-39158021473543f4ac35ef0e69fd1d35
Source dataset
uspto-grants-2002_11
Patent number
US06476030B1

Reaction notes

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