Methyl iodide → 4-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridine

HRID 639780Notes

Reaction equation

HRID 639780 reaction equation
[CH3:1][N:2]1[C:6]([C:7]2[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=2)=[N:5][NH:4][C:3]1=[S:13].I[CH3:15]>[OH-].[Na+].C(O)C>[CH3:1][N:2]1[C:3]([S:13][CH3:15])=[N:4][N:5]=[C:6]1[C:7]1[CH:12]=[CH:11][N:10]=[CH:9][CH:8]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 7385474-methyl-5-(pyridin-4-yl)-4H-1,2,4-triazole-3-thiol

Product 1

HCID 8659874-(4-Methyl-5-(methylthio)-4H-1,2,4-triazol-3-yl)pyridineYield 94%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

To a solution of 4-Methyl-5-pyridin-4-yl-2,4-dihydro-[1,2,4]triazole-3-thione (1000 mg, 5.20 mmol) in 1M sodium hydroxide (10 mL), added a solution of iodomethane (0.52 mL, 8.32 mmol) in ethanol (3 mL). Stirred at RT overnight. Extracted into 200 mL dichloromethane and washed with brine (50 mL). Dried over anhydrous sodium sulfate, filtered and concentrated in vacuo to yield title compound (1.00 g, 94% yield). 1H-NMR (CDCl3) δ (ppm): 8.81 (d, 2H), 7.62 (d, 2H), 3.68 (s, 3H), 2.82 (s, 3H).

Workup

  1. extractionExtracted into 200 mL dichloromethane
  2. washwashed with brine (50 mL)
  3. dry with materialDried over anhydrous sodium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-6758800d16a04f16869d642e6b765ce4
Source dataset
uspto-grants-2010_04
Patent number
US07691892B2

Reaction notes

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