Methyl iodide → 2-Methoxy-4-(4-methyl-5-methylsulfanyl-4h-[1,2,4]triazol-3-yl)-pyridine

HRID 500545Notes

Reaction equation

HRID 500545 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]([CH3:15])[C:11]([SH:14])=[N:12][N:13]=2)[CH:6]=[CH:5][N:4]=1.I[CH3:17]>[OH-].[Na+].C(O)C>[CH3:1][O:2][C:3]1[CH:8]=[C:7]([C:9]2[N:10]([CH3:15])[C:11]([S:14][CH3:17])=[N:12][N:13]=2)[CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 2

HCID 6328Methyl iodideHCID 178488243HCID 178488243, compound

Product 1

HCID 248517082-Methoxy-4-(4-methyl-5-methylsulfanyl-4h-[1,2,4]triazol-3-yl)-pyridineYield 97.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 14798Sodium HydroxideSolvent

Procedure

The title compound of example 24.1 (21.30 g, 95.83 mmol) was set stirring in 1 M sodium hydroxide in a cold water bath. Iodomethane (21.76 g, 153.3 mmol) in ethanol (63 mL) was added to the reaction. As the reaction progressed, solid began to precipitate out. The reaction was allowed to stir at RT for 12 hours. The reaction mixture was extracted with dichloromethane and the organic extracts were washed with brine, dried and concentrated to afford the title compound as a white solid (22 g, 97%).

Workup

  1. customto precipitate out
  2. extractionThe reaction mixture was extracted with dichloromethane
  3. washthe organic extracts were washed with brine
  4. customdried
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-61e32176a0d44470aed2709f2325e35b
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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