Potassium Carbonate → HCID 68708425, compound

HRID 1712932Notes

Reaction equation

HRID 1712932 reaction equation
[NH:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1.I[C:11]1[CH:18]=[CH:17][CH:16]=[CH:15][C:12]=1[C:13]#[N:14].N1CCC[C@H]1C(O)=O.C(=O)([O-])[O-].[K+].[K+]>CS(C)=O.CCOC(C)=O.[Cu]I>[C:13]([C:12]1[CH:15]=[CH:16][CH:17]=[CH:18][C:11]=1[N:1]1[CH:5]=[C:4]([C:6]([O:8][CH3:9])=[O:7])[N:3]=[CH:2]1)#[N:14]

Participants

8

Reactant 4

HCID 11430Potassium CarbonateHCID 145742L-ProlineHCID 27593582-IodobenzonitrileHCID 178418785HCID 178418785, compound

Product 1

HCID 68708425HCID 68708425, compound

Reagents, catalysts & solvents 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)CatalystHCID 679Dimethyl SulfoxideSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of methyl 1H-imidazole-4-carboxylate (400 mg, 0.003 mol), 2-iodobenzonitrile (800 mg, 0.0035 mol), L-proline (0.073 g, 0.00063 mol), potassium carbonate (0.88 g, 0.0063 mol) and copper(I) iodide (0.060 g, 0.00032 mol) in DMSO (8 mL) was allowed to stir and heated at 90° C. in a sealed tube overnight. The mixture was diluted with EtOAc, washed with water and brine, dried over Na2SO4, filtered and concentrated. The residue was purified by column chromatography to afford methyl 1-(2-cyanophenyl)-1H-imidazole-4-carboxylate. LCMS: (FA) ES+ 228.1

Workup

  1. washwashed with water and brine
  2. dry with materialdried over Na2SO4
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customThe residue was purified by column chromatography

Sources & evidence

ORD record
ord-f2186df6c0084a5f98ad69b9a9dddd1a
Source dataset
uspto-grants-2010_09
Patent number
US07795249B2

Reaction notes

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