Water → HCID 21097229, compound

HRID 2109229Notes

Reaction equation

HRID 2109229 reaction equation
[CH2:1]([C:3]1[NH:4][C:5]([CH:8]=[O:9])=[CH:6][N:7]=1)[CH3:2].[CH2:10](I)[CH3:11].C([O-])([O-])=O.[K+].[K+].O>CN(C=O)C.C(Cl)Cl.CO>[CH2:10]([N:4]1[C:5]([CH:8]=[O:9])=[CH:6][N:7]=[C:3]1[CH2:1][CH3:2])[CH3:11].[CH2:10]([N:7]1[CH:6]=[C:5]([CH:8]=[O:9])[N:4]=[C:3]1[CH2:1][CH3:2])[CH3:11]

Participants

9

Reactant 4

HCID 962WaterHCID 6340IodoethaneHCID 11430Potassium CarbonateHCID 27374212-ethyl-1H-imidazole-5-carbaldehyde

Product 2

HCID 21097229HCID 21097229, compoundYield 43%HCID 21097230HCID 21097230, compoundYield 19%

Reagents, catalysts & solvents 3

HCID 887MethanolSolventHCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To 2-ethyl-5-formylimidazole (200 mg; 1.611 mmol) in 2 mL of DMF was added 0.132 mL (1.65 mmol) of EtI and 224 mg (1.62 mmol) of K2CO3. The mixture was stirred for 12 h, and then it was poured into water and extracted twice with EtOAc. The organic extracts were washed with brine, dried over Na2SO4, filtered and concentrated. Chromatography (0.5-2.0% MeOH in CH2Cl2) provided 46 mg (0.30 mmol; 19%) of 1,2-diethyl-5-formyl-1H-imidazole and 106 mg (0.69 mmol; 43%) of 1,2-diethyl-4-formyl-1H-imidazole.

Workup

  1. extractionextracted twice with EtOAc
  2. washThe organic extracts were washed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-af0428f6883f46a5ac1dea3cff373fc0
Source dataset
uspto-grants-2009_04
Patent number
US07514458B2

Reaction notes

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