Imidazole → Methyl 4-(imidazol-1-ylmethyl)-3-methoxybenzoate

HRID 2053997Notes

Reaction equation

HRID 2053997 reaction equation
[NH:1]1[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].Br[CH2:9][C:10]1[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=1[O:20][CH3:21]>O1CCCC1>[N:1]1([CH2:9][C:10]2[CH:19]=[CH:18][C:13]([C:14]([O:16][CH3:17])=[O:15])=[CH:12][C:11]=2[O:20][CH3:21])[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 24758Sodium hydrideHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoate

Product 1

HCID 69314851Methyl 4-(imidazol-1-ylmethyl)-3-methoxybenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

0.39 g (5.8 mmol) of imidazole are dissolved in 50 mL of tetrahydrofuran and, after the addition of 305.6 mg (6.4 mmol) of sodium hydride (50% in oil), stirred for 10 minutes at ambient temperature. Then 1.5 g (5.8 mmol) of methyl 4-(bromomethyl)-3-methoxybenzoate are added and the mixture is stirred for a further 16 hours. The solvent is distilled off, decomposed with water and extracted with ethyl acetate. The combined organic extracts are dried and concentrated by evaporation. Yield: 1.4 g (99%); C13H14N2O3 (246.268); mass spectrum: (M+H)+=247

Workup

  1. stirringthe mixture is stirred for a further 16 hours
  2. distillationThe solvent is distilled off
  3. extractionextracted with ethyl acetate
  4. customThe combined organic extracts are dried
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-c81597c504824600a960c867b9d30256
Source dataset
uspto-grants-2008_02
Patent number
US07326791B2

Reaction notes

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