Imidazole → HCID 15837878, compound

HRID 1081864Notes

Reaction equation

HRID 1081864 reaction equation
Br[CH2:2][C:3]1[CH:19]=[C:18]([Cl:20])[CH:17]=[CH:16][C:4]=1[O:5][C:6]1[C:15]2[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=2)[CH:9]=[CH:8][CH:7]=1.[NH:21]1[CH:25]=[CH:24][N:23]=[CH:22]1.C(=O)([O-])[O-].[Cs+].[Cs+]>C(#N)C>[Cl:20][C:18]1[CH:17]=[CH:16][C:4]([O:5][C:6]2[C:15]3[C:10](=[CH:11][CH:12]=[CH:13][CH:14]=3)[CH:9]=[CH:8][CH:7]=2)=[C:3]([CH:19]=1)[CH2:2][N:21]1[CH:25]=[CH:24][N:23]=[CH:22]1

Participants

5

Reactant 3

HCID 795ImidazoleHCID 10796Cesium carbonateHCID 15837892HCID 15837892, compound

Product 1

HCID 15837878HCID 15837878, compoundYield 70.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

1-(2-Bromomethyl-4-chlorophenoxy)naphthalene (400 mg) from Example 3 was dissolved in acetonitrile (20 ml), followed by addition of imidazole (235 mg) and cesium carbonate (1.1 g) under reflux for 10 minutes. After leaving the solution to stand at room temperature, the solvent was removed under reduced pressure. The residue was purified by chromatography on a silica gel column (methylene chloride:methanol=99:1) to give the title compound (270 mg; 70%). The purity of the compound was determined by HPLC, which was of 99.9%.

Workup

  1. temperatureunder reflux for 10 minutes
  2. customAfter leaving the solution
  3. customto stand at room temperature
  4. customthe solvent was removed under reduced pressure
  5. customThe residue was purified by chromatography on a silica gel column (methylene chloride:methanol=99:1)

Sources & evidence

ORD record
ord-09420396786c4734b4c01d58ae390780
Source dataset
uspto-grants-1996_12
Patent number
US05587392

Reaction notes

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