Cesium carbonate → HCID 86586167, compound

HRID 433587Notes

Reaction equation

HRID 433587 reaction equation
Cl[CH2:2][C:3]1[N:4]=[CH:5][N:6]([C:8]2[CH:13]=[CH:12][C:11]([Cl:14])=[C:10]([Cl:15])[CH:9]=2)[CH:7]=1.[NH:16]1[CH:20]=[CH:19][N:18]=[C:17]1[CH:21]=[O:22].C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C>[Cl:15][C:10]1[CH:9]=[C:8]([N:6]2[CH:7]=[C:3]([CH2:2][N:16]3[CH:20]=[CH:19][N:18]=[C:17]3[CH:21]=[O:22])[N:4]=[CH:5]2)[CH:13]=[CH:12][C:11]=1[Cl:14]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 249551H-imidazole-2-carbaldehydeHCID 234450324-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole

Product 1

HCID 86586167HCID 86586167, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

4-Chloromethyl-1-(3,4-dichloro-phenyl)-1H-imidazole (1.31 g, 5.0 mmol) was dissolved in DMF (10 ml), 2-imidazolecarboxaldehyde (0.48 g, 5.0 mmol) and cesium carbonate (0.82 g, 2.5 mmol) was added and the resulting mixture was stirred at 60° C. for 12 h. After evaporation of the solvent the residue was dissolved in AcOEt and washed with H2O. The organic phase was dried (Na2SO4), concentrated and chromatographed [silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)] to obtain 0.98 g (61%) of the title compound as an off-white solid. Mp. 130-131° C. (CH2Cl2/iPr2O), MS: m/e=320 (M+).

Workup

  1. customAfter evaporation of the solvent the residue
  2. dissolutionwas dissolved in AcOEt
  3. washwashed with H2O
  4. dry with materialThe organic phase was dried (Na2SO4)
  5. concentrationconcentrated
  6. customchromatographed
  7. wash[silica, elution with gradient CH2Cl2 to 100% (CH2Cl2/MeOH=9:1)]

Sources & evidence

ORD record
ord-ddadb30fbc9d4f52b3831f46ef27eae6
Source dataset
uspto-grants-2003_12
Patent number
US06667335B2

Reaction notes

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