Methyl iodide → HCID 21833724, compound

HRID 1741075Notes

Reaction equation

HRID 1741075 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[CH:4][C:3]=1[CH3:13].[H-].[Na+].I[CH3:17]>C1COCC1>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:12]([CH3:17])[CH:11]=[CH:10][N:9]=2)=[CH:4][C:3]=1[CH3:13]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 21833745HCID 21833745, compound

Product 1

HCID 21833724HCID 21833724, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-(4-Bromo-3-methylphenyl)imidazole (D88, 900 mg; 3.8 mmol) was dissolved in dry THF (30 ml) under argon and treated with sodium hydride (114 mg of an 80% dispersion in mineral oil; 3.8 mmol). After stirring for 30 minutes, iodomethane (237 μl; 3.8 mmol) was added and stirring continued for 18 hours. Evaporated in vacuo, the residue partitioned between water and CHCl3, the organic phase then dried over Na2SO4, filtered and evaporated in vacuo. The residue was purified by flash silica gel chromatography using CHCl3 as eluant to yield the title compound as a clear, colourless gum (600 mg; 63%).

Workup

  1. stirringstirring
  2. waitcontinued for 18 hours
  3. customEvaporated in vacuo
  4. customthe residue partitioned between water and CHCl3
  5. dry with materialthe organic phase then dried over Na2SO4
  6. filtrationfiltered
  7. customevaporated in vacuo
  8. customThe residue was purified by flash silica gel chromatography

Sources & evidence

ORD record
ord-de9767d293aa4bae9dbaabfe8c065a27
Source dataset
uspto-grants-1999_10
Patent number
US05972951

Reaction notes

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