Iodoethane → 1-Ethyl-5-methyl-1H-imidazole-4-carbaldehyde

HRID 491414Notes

Reaction equation

HRID 491414 reaction equation
[CH3:1][C:2]1[NH:6][CH:5]=[N:4][C:3]=1[CH:7]=[O:8].[H-].[Na+].[CH2:11](I)[CH3:12]>C1COCC1.CN(C=O)C>[CH2:11]([N:6]1[C:2]([CH3:1])=[C:3]([CH:7]=[O:8])[N:4]=[CH:5]1)[CH3:12]

Participants

6

Reactant 3

HCID 6340IodoethaneHCID 24758Sodium hydrideHCID 27958875-Methyl-1H-imidazole-4-carbaldehyde

Product 1

HCID 576783131-Ethyl-5-methyl-1H-imidazole-4-carbaldehydeYield 33.2%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8028TetrahydrofuranSolvent

Procedure

5-Methyl-1H-imidazole-4-carbaldehyde (940 mg, 8.5 mmol) was dissolved in THF (40 ml) with DMF (5 ml). NaH (380 mg of a 60% dispersion in mineral oil) was added carefully and the reaction mixture was allowed to stir for 5 min. under nitrogen. Ethyl iodide (1.65 g, 9.7 mmol) was added and it was allowed to stir for 1 h, at which time the reaction was judged complete. The solvent was removed under vacuum, and the crude was purified on silica eluted with 100% ethyl acetate—1% MeOH/ethyl acetate to yield the title product (390 mg) as the main isomer. MS (ESI-POS): [M+H]+=139.

Workup

  1. stirringto stir for 1 h, at which time the reaction
  2. customThe solvent was removed under vacuum
  3. customthe crude was purified on silica
  4. washeluted with 100% ethyl acetate—1% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-c1fa8d5ef23c4dcfab3f18d3f5f2af37
Source dataset
uspto-grants-2009_05
Patent number
US07531542B2

Reaction notes

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