Methyl iodide → Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

HRID 2074071Notes

Reaction equation

HRID 2074071 reaction equation
[N+:1]([C:4]1[N:5]=[C:6]([C:9]([O:11][CH2:12][CH3:13])=[O:10])[NH:7][CH:8]=1)([O-:3])=[O:2].[C:14](=O)([O-])[O-].[K+].[K+].IC.C1CCCCC1.C(OCC)(=O)C>CC(C)=O>[CH3:14][N:7]1[CH:8]=[C:4]([N+:1]([O-:3])=[O:2])[N:5]=[C:6]1[C:9]([O:11][CH2:12][CH3:13])=[O:10]

Participants

6

Reactant 4

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 21867204Cyclohexane ethylacetateHCID 178470305HCID 178470305, compound

Product 1

HCID 2758876Ethyl 1-methyl-4-nitroimidazole-2-carboxylate

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Conditions

Temperature
60 °C

Procedure

6.80 g (36.7 mmol) of ethyl 4-nitro-1H-imidazole-2-carboxylate are dissolved in 140 ml of acetone, and 11.2 g (80.8 mmol) of potassium carbonate and 4.57 ml (73.5 mmol) of iodomethane are added. The mixture is then stirred at 60° C. for 4 h. According to TLC (cyclohexane/ethyl acetate 2:1), the starting material has been converted completely. After cooling, the mixture is filtered, the residue is washed with dichloromethane and the filtrate is freed from the solvent. The solid obtained is dried in vacuo.

Workup

  1. temperatureAfter cooling
  2. filtrationthe mixture is filtered
  3. washthe residue is washed with dichloromethane
  4. customThe solid obtained
  5. customis dried in vacuo

Sources & evidence

ORD record
ord-b793f13c47284608a67f50fde8aaafc1
Source dataset
uspto-grants-2011_04
Patent number
US07919489B2

Reaction notes

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