Methyl iodide → 1-Methyl-2-phenyl-1H-imidazole

HRID 1895844Notes

Reaction equation

HRID 1895844 reaction equation
[C:1]1([C:7]2[NH:8][CH:9]=[CH:10][N:11]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[H-].[Na+].[CH3:14]I>C1COCC1>[CH3:14][N:11]1[CH:10]=[CH:9][N:8]=[C:7]1[C:1]1[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 695912-Phenylimidazole

Product 1

HCID 770251-Methyl-2-phenyl-1H-imidazole

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

2-phenylimidazole (5 g) was taken into 150 ml of THF. To this solution 2.3 g of NaH were added. After refluxing for an hour under nitrogen 5.9 g of methyl iodide were added. The reaction mixture was refluxed for another 3 hours under nitrogen and then quenched with 5 ml of water. The solution was evaporated to dryness, and 200 ml of ethylacetate were added. The solution was washed with water and dried over MgSO4. The resulting product was column purified on a SiO2 using dichloromethane methane solvent mixture (95:5). The purified product is colourless oil. 1H NMR (CDCl3) δ 7.55 (2H, d, J=4.5 Hz), 7.34(3H, dd J=5.3, 1.76), 7.01 (1H, d J=1.2 Hz), 6.85 (1H, d 1.2 Hz), 3.6 (3H, s).

Workup

  1. additionwere added
  2. temperatureThe reaction mixture was refluxed for another 3 hours under nitrogen
  3. customquenched with 5 ml of water
  4. customThe solution was evaporated to dryness, and 200 ml of ethylacetate
  5. additionwere added
  6. washThe solution was washed with water
  7. dry with materialdried over MgSO4
  8. custompurified on a SiO2

Sources & evidence

ORD record
ord-908edd2757e74873bd088444b8bf6efb
Source dataset
uspto-grants-2013_08
Patent number
US08518557B2

Reaction notes

Loading…