Isopropyl iodide → Methyl 1-(propan-2-yl)-1H-imidazole-4-carboxylate

HRID 2355288Notes

Reaction equation

HRID 2355288 reaction equation
[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][NH:10][CH:11]=1)=[O:6].[CH:12](I)([CH3:14])[CH3:13]>CN(C)C=O>[CH3:3][O:4][C:5]([C:7]1[N:8]=[CH:9][N:10]([CH:12]([CH3:14])[CH3:13])[CH:11]=1)=[O:6]

Participants

5

Reactant 3

HCID 6362Isopropyl iodideHCID 24758Sodium hydrideHCID 178418785HCID 178418785, compound

Product 1

HCID 20769004Methyl 1-(propan-2-yl)-1H-imidazole-4-carboxylateYield 17.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

Add sodium hydride (2.87 g, 71.7 mmol, 60% in mineral oil) portion-wise over 10 minutes to a cooled (0° C.) solution of 1H-imidazole-4-carboxylic acid methyl ester (6.03 g, 47.8 mmol) in dimethylformamide (150 ml). Remove the cooling bath and stir at room temperature for 4.5 hrs. Cool the mixture to 0° C. and add isopropyl iodide (8.94 g, 52.6 mmol) dropwise over 10 min. Remove the cooling bath and stir at room temperature for 20 hrs. Quench the mixture with saturated aqueous ammonium chloride and extract with ethyl acetate (3×). Wash the combined extracts with brine, dry over sodium sulfate, filter and concentrate under reduced pressure to give an oil. Purify the oil by flash chromatography (silica gel) eluting with 25% acetone/hexanes to provide the product as an oil (1.41 g, 8.4 mmol, 17% yield). M/S (m/z): 169 (M+H).

Workup

  1. customRemove the cooling bath
  2. temperatureCool the mixture to 0° C.
  3. customRemove the cooling bath
  4. stirringstir at room temperature for 20 hrs
  5. customQuench the mixture with saturated aqueous ammonium chloride
  6. extractionextract with ethyl acetate (3×)
  7. washWash the combined extracts with brine
  8. dry with materialdry over sodium sulfate
  9. filtrationfilter
  10. concentrationconcentrate under reduced pressure
  11. customto give an oil
  12. customPurify the oil by flash chromatography (silica gel)
  13. washeluting with 25% acetone/hexanes

Sources & evidence

ORD record
ord-aabb3aa26c8347adafa521581d27e637
Source dataset
uspto-grants-2010_07
Patent number
US07754742B2

Reaction notes

Loading…