Methyl iodide → 2-Amino-1-methylbenzimidazole

HRID 1896341Notes

Reaction equation

HRID 1896341 reaction equation
[NH2:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.[OH-].[K+].[CH3:13]I>CC(C)=O.C(OCC)(=O)C>[CH3:13][N:3]1[C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=[C:2]1[NH2:1]

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 136242-AminobenzimidazoleHCID 14797Potassium Hydroxide

Product 1

HCID 741872-Amino-1-methylbenzimidazole

Reagents, catalysts & solvents 2

HCID 180AcetoneSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 2-aminobenzimidazole (3.0 g, 0.0225 mol) in acetone (30 ml) was added KOH (6.32 g, 0.112 mol) followed by methyl iodide (3.51 g, 0.025 mol) and stirred at room temperature for 10 min. The reaction mixture was diluted with ethyl acetate and the organic layer washed with water, brine and dried over anhydrous Na2SO4 to afford crude residue which was column purified to yield the desired product: 1H NMR (300 MHz, DMSO-d6) δ 3.47 (s, 3H), 6.34 (br s, 2H), 6.82-6.92 (m, 2H), 7.06-7.09 (m, 2H); ESI-MS (m/z) 148.49 (M+H)+.

Workup

  1. washthe organic layer washed with water, brine
  2. dry with materialdried over anhydrous Na2SO4
  3. customto afford crude residue which
  4. custompurified

Sources & evidence

ORD record
ord-7df69c4ae4c04d379a5aae8a89654da2
Source dataset
uspto-grants-2013_08
Patent number
US08518955B2

Reaction notes

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