Potassium Iodide → HCID 23139317, compound

HRID 1171704Notes

Reaction equation

HRID 1171704 reaction equation
Br[CH2:2][C:3]([O:5][CH2:6][CH3:7])=[O:4].[C:8](=[O:11])([O-])[O-].[K+].[K+].[I-].[K+].[C:16](#[N:18])[CH3:17].O.[C:20](#[N:22])C>>[CH2:6]([O:5][C:3](=[O:4])[CH2:2][N:18]1[CH:16]=[C:17]([CH:8]=[O:11])[N:22]=[CH:20]1)[CH3:7]

Participants

6

Reactant 5

HCID 4875Potassium IodideHCID 6342AcetonitrileHCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 18373917Acetonitrile--water (1/1)

Product 1

HCID 23139317HCID 23139317, compoundYield 44%

Procedure

To a solution of 1H-imidazole-4(5)-carbaldehyde (5.5 g) in acetonitrile (100 ml) were added ethyl bromoacetate (7.65 ml), potassium carbonate (15.8 g) and potassium iodide (11.4 g) with stirring. The mixture was stirred at 50° C. for 3.5 hours, and after cooling, precipitates were removed by filtration, and the filtrate was concentrated under reduced pressure. The residue thus obtained was purified successively by silica gel chromatography using dichloromethane and methanol (10:1) as an eluent and by preparative HPLC (YMC-Pack ODS-A; YMC, eluent: acetonitrile/water, 15/85, v/v) to afford ethyl(4-formyl-1H-imidazol-1-yl)acetate (4.60 g, yield: 44%) as the more mobile isomer, and the title compound (1.95 g, yield: 19%) as the less mobile isomer, both as yellow oils respectively. The less mobile, title isomer: 1H NMR (500 MHz, CDCl3) δ ppm: 1.30 (3H, t, J=7.0), 4.26 (2H, q, J=7.0), 5.05 (2H, s), 7.68 (1H, s), 7.84 (1H, s), 9.75 (1H, s).

Workup

  1. stirringThe mixture was stirred at 50° C. for 3.5 hours
  2. temperatureafter cooling
  3. customprecipitates
  4. customwere removed by filtration
  5. concentrationthe filtrate was concentrated under reduced pressure
  6. customThe residue thus obtained
  7. customwas purified successively by silica gel chromatography

Sources & evidence

ORD record
ord-060151cb9f804516b05df0adeab45c72
Source dataset
uspto-grants-2010_11
Patent number
US07829580B2

Reaction notes

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