Methyl iodide → 2-(3-Hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazole

HRID 545327Notes

Reaction equation

HRID 545327 reaction equation
[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[NH:14][C:15]([I:19])=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6].[H-].[Na+].I[CH3:23]>CN(C=O)C>[CH2:1]([C:7]1[CH:8]=[C:9]([C:13]2[N:14]([CH3:23])[C:15]([I:19])=[C:16]([I:18])[N:17]=2)[CH:10]=[CH:11][CH:12]=1)[CH2:2][CH2:3][CH2:4][CH2:5][CH3:6]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 671332282-(3-hexyl-phenyl)-4,5-diiodo-1H-imidazole

Product 1

HCID 671329302-(3-Hexyl-phenyl)-4,5-diiodo-1-methyl-1H-imidazoleYield 87%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of 8.45 g (17.6 mmol) of 2-(3-hexyl-phenyl)-4,5-diiodo-1H-imidazole in 150 ml of DMF was treated at 0° C. with 0.806 g (18.5 mmol) of sodium hydride (55% dispersion in mineral oil); 15 min later, a solution of 1.52 ml=3.47 g (24.2 mmol) of iodomethane in 25 ml of DMF was added drop by drop at 0° C. After 2 hours, the reaction mixture was poured into crashed ice and extracted twice with EtOAc; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated. The residue was purified by flash column chromatography (n-heptane/EtOAc 1:0 to 4:1) to give 7.52 g (87%) of the title compound as light red oil. MS: 495.1 (MH+).

Workup

  1. additionthe reaction mixture was poured
  2. extractionextracted twice with EtOAc
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated
  7. customThe residue was purified by flash column chromatography (n-heptane/EtOAc 1:0 to 4:1)

Sources & evidence

ORD record
ord-35496834e67e4fdfa287d2110d3eefd8
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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