Methyl iodide → HCID 86714662, compound

HRID 1409435Notes

Reaction equation

HRID 1409435 reaction equation
[CH2:1]([C:5]1[NH:6][CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4].[C:14]([O-])([O-])=O.[Cs+].[Cs+].CI>CC(C)=O>[CH2:1]([C:5]1[N:6]([CH3:14])[CH:7]=[C:8]([C:10]([O:12][CH3:13])=[O:11])[N:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 178441776HCID 178441776, compound

Product 1

HCID 86714662HCID 86714662, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

Into flask containing a solution of methyl 2-butyl-1H-imidazole-4-carboxylate (1.2 g, 6.6 mmol) in acetone (40 ml), Cs2CO3 (6.5 g, 19.8 mmol) and methyl iodide (0.5 ml, 6.6 mmol) were added. The reaction mixture was stirred at RT for 4 h and the solvent was evaporated. The residue was diluted with water and extracted with EtOAc. The organic layer was concentrated and purified with flash chromatography. Yield 500 mg. 1H-NMR (400 MHz; CDCl3): δ 0.937 (t, 3H), 1.35-1.44 (m, 2H), 1.68-1.75 (m, 2H), 2.69 (t, 2H), 3.62 (s, 3H), 3.86 (s, 3H), 7.50 (s, 1H).

Workup

  1. additionwere added
  2. customthe solvent was evaporated
  3. additionThe residue was diluted with water
  4. extractionextracted with EtOAc
  5. concentrationThe organic layer was concentrated
  6. custompurified with flash chromatography

Sources & evidence

ORD record
ord-1884fc4950244d74a3f0d109d304eda7
Source dataset
uspto-grants-2014_12
Patent number
US08921378B2

Reaction notes

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