Methyl iodide → HCID 66887984, compound

HRID 252394Notes

Reaction equation

HRID 252394 reaction equation
[CH2:1]([O:3][C:4](=[O:13])[C:5]([C:8]1[N:9]=[CH:10][NH:11][CH:12]=1)([CH3:7])[CH3:6])[CH3:2].[H-].[Na+].CI.[C:18](=O)([O-])O.[Na+]>CN(C)C=O>[CH2:1]([O:3][C:4](=[O:13])[C:5]([CH3:7])([C:8]1[N:9]=[CH:10][N:11]([CH3:18])[CH:12]=1)[CH3:6])[CH3:2]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 516892Sodium BicarbonateHCID 178471274HCID 178471274, compound

Product 1

HCID 66887984HCID 66887984, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
60 °C

Procedure

A solution of 1.82 g of 2-(1H-imidazol-4-yl)-2-methyl-propionic acid ethyl ester [CAS 21149-99-5] in 20 ml of dry N,N-dimethylformamide is treated with 0.480 g sodium hydride (60% dispersion). The mixture is stirred for 30 minutes at 60° C. 0.81 ml of methyl iodide are added and the mixture stirred for 4 hours at 60° C. The reaction mixture is poured onto saturated aqueous sodium hydrogencarbonate solution and extracted with tert-butyl methyl ether (3×). The combined extracts are washed with brine, dried over sodium sulphate and concentrated by evaporation. Flash chromatography (SiO2 60F) of the residue provides the title compound which is identified on the basis of its Rf-value.

Workup

  1. stirringthe mixture stirred for 4 hours at 60° C
  2. extractionextracted with tert-butyl methyl ether (3×)
  3. washThe combined extracts are washed with brine
  4. dry with materialdried over sodium sulphate
  5. concentrationconcentrated by evaporation

Sources & evidence

ORD record
ord-f952b75def904d21a206609b93a249e6
Source dataset
uspto-grants-2011_01
Patent number
US07868036B2

Reaction notes

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