Methyl iodide → Methyl 1-methyl-1H-[1,2,4]triazole-3-carboxylate

HRID 244637Notes

Reaction equation

HRID 244637 reaction equation
[NH:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1.[H-].[Na+].[CH3:12]I>C1COCC1>[CH3:12][N:1]1[CH:5]=[N:4][C:3]([C:6]([O:8][CH3:9])=[O:7])=[N:2]1

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 178499122HCID 178499122, compound

Product 1

HCID 19778899Methyl 1-methyl-1H-[1,2,4]triazole-3-carboxylateYield 26.1%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of methyl 1H-1,2,4-triazole-3-carboxylate (1 g) and sodium hydride (0.315 g) in anhydrous THF (30 ml) was heated at reflux for 7 h under nitrogen. The reaction was cooled to RT and methyl iodide (1.12 g) was added. The reaction was heated at reflux overnight. The solvent was evaporated and water (10 ml) was added. This was extracted with DCM, the organic layer collected and evaporated to dryness. The residue was dissolved in methanol:DMSO (6 ml, 1:1) and purified by mass directed preparative HPLC (Method A) to give title compound (0.290 g).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 7 h under nitrogen
  3. temperatureThe reaction was heated
  4. temperatureat reflux overnight
  5. customThe solvent was evaporated
  6. additionwater (10 ml) was added
  7. extractionThis was extracted with DCM
  8. customthe organic layer collected
  9. customevaporated to dryness
  10. dissolutionThe residue was dissolved in methanol
  11. customDMSO (6 ml, 1:1) and purified by mass

Sources & evidence

ORD record
ord-892122e8e873458792888c577c39726d
Source dataset
uspto-grants-2014_02
Patent number
US08658635B2

Reaction notes

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