Ethanol → 1-Methyl-4-(4-methyl-5-methylsulfanyl-4h-[1,2,4]triazol-3-yl)-1h-pyridin-2-one

HRID 500552Notes

Reaction equation

HRID 500552 reaction equation
[SH:1][C:2]1[N:3]([CH3:15])[C:4]([C:7]2[CH:12]=[CH:11][N:10]([CH3:13])[C:9](=[O:14])[CH:8]=2)=[N:5][N:6]=1.[OH-].[Na+].[CH2:18](O)C.IC>O>[CH3:13][N:10]1[CH:11]=[CH:12][C:7]([C:4]2[N:3]([CH3:15])[C:2]([S:1][CH3:18])=[N:6][N:5]=2)=[CH:8][C:9]1=[O:14]

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178481695HCID 178481695, compound

Product 1

HCID 248520611-Methyl-4-(4-methyl-5-methylsulfanyl-4h-[1,2,4]triazol-3-yl)-1h-pyridin-2-oneYield 78%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

The title compound from example 32.1 (600 mg, 2.7 mmol) was dissolved in a solution of sodium hydroxide (216 mg, 5.4 mmol) and water (5 mL). When a clear, uniform solution was observed ethanol (6 mL) was added, followed by iodomethane (268 μL, 4.3 mmol). The reaction was stirred at room temperature for 6 h. The reaction mixture was then diluted with water and extracted four times with chloroform. The organic phase was dried over magnesium sulfate, filtered and concentrated to yield the title compound (yellowish solid, 500 mg, 78%).

Workup

  1. additionwas added
  2. extractionextracted four times with chloroform
  3. dry with materialThe organic phase was dried over magnesium sulfate
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-21cd996aec87452e82cc17978abd2a69
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

Loading…