Methyl iodide → HCID 12582444, compound

HRID 1828578Notes

Reaction equation

HRID 1828578 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[CH:10][NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([Cl:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[CH3:20]I.[H-].[Na+]>CN(C=O)C>[Cl:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[CH:10][N:9]([CH3:20])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 124673074,5-Bis(4-chlorophenyl)-1H-imidazole

Product 1

HCID 12582444HCID 12582444, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4,5-di-(4-chlorophenyl)imidazole (300 mg, 1.0 mmol) from Step A and methyl iodide (0.10 mL, 2.0 mmol) in DMF (5 mL) was added sodium hydride (80 mg 60% in mineral oil, 1.5 mmol) all at once at rt. After stirring for 1 hr, the reaction was quenched into water and extracted twice with ethyl acetate. The organic layers were washed with brine, dried over sodium sulfate, and evaporated. The residue was purified by flash chromatography (10% methylene chloride, 30% ethyl acetate in hexanes) to provide the title compound as a white solid.

Workup

  1. customthe reaction was quenched into water
  2. extractionextracted twice with ethyl acetate
  3. washThe organic layers were washed with brine
  4. dry with materialdried over sodium sulfate
  5. customevaporated
  6. customThe residue was purified by flash chromatography (10% methylene chloride, 30% ethyl acetate in hexanes)

Sources & evidence

ORD record
ord-193d661771e446b1bb3fb69ee775193a
Source dataset
uspto-grants-2006_06
Patent number
US07057051B2

Reaction notes

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