Potassium Carbonate → HCID 18786373, compound

HRID 1418467Notes

Reaction equation

HRID 1418467 reaction equation
[CH3:1][C:2]1[NH:3][CH:4]=[CH:5][N:6]=1.[I:7][C:8]1[CH:15]=[CH:14][C:11]([CH2:12]Br)=[CH:10][CH:9]=1.C(=O)([O-])[O-].[K+].[K+]>C(#N)C>[CH3:1][C:2]1[N:3]([CH2:12][C:11]2[CH:14]=[CH:15][C:8]([I:7])=[CH:9][CH:10]=2)[CH:4]=[CH:5][N:6]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 127492-MethylimidazoleHCID 9542584-Iodobenzyl bromide

Product 1

HCID 18786373HCID 18786373, compoundYield 44%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methylimidazole (0.66 g, 8.0 mmol), 4-iodobenzyl bromide (J. Am. Chem. Soc, 1949, 71, 3360) (2.38 g, 8.0 mmol) and potassium carbonate (2.21 g, 16 mmol) in acetonitrile (100 ml) was stirred at reflux for 15 hrs. After cooling, precipitates were filtered off and the filtrate was concentrated to dryness. The residue was partitioned between ether (100 ml) and water (100 ml). The ethereal layer was separated, washed with brine (100 ml), dried (magnesium sulfate) and concentrated. Purification by column chromatography (silica-gel, 50 g; methanol in dichloro-methane, increasing the ratio of methanol from 0% to 5%) yielded the titled compound (1.05 g, 44%).

Workup

  1. temperatureat reflux for 15 hrs
  2. temperatureAfter cooling
  3. customprecipitates
  4. filtrationwere filtered off
  5. concentrationthe filtrate was concentrated to dryness
  6. customThe residue was partitioned between ether (100 ml) and water (100 ml)
  7. customThe ethereal layer was separated
  8. washwashed with brine (100 ml)
  9. dry with materialdried (magnesium sulfate)
  10. concentrationconcentrated
  11. customPurification by column chromatography (silica-gel, 50 g
  12. temperaturemethanol in dichloro-methane, increasing the ratio of methanol from 0% to 5%)

Sources & evidence

ORD record
ord-611d66e2b73a487d8192997610ca65b3
Source dataset
uspto-grants-1999_03
Patent number
US05883106

Reaction notes

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