Ethanol → 4-[4-Methyl-5-(methylthio)-4h-1,2,4-triazol-3-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}pyridin-2(1h)-one

HRID 500542Notes

Reaction equation

HRID 500542 reaction equation
[SH:1][C:2]1[N:3]([CH3:22])[C:4]([C:7]2[CH:12]=[CH:11][N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:20])([CH3:19])[CH3:18])[C:9](=[O:21])[CH:8]=2)=[N:5][N:6]=1.[OH-].[Na+].[CH2:25](O)C.IC>O>[CH3:22][N:3]1[C:2]([S:1][CH3:25])=[N:6][N:5]=[C:4]1[C:7]1[CH:12]=[CH:11][N:10]([CH2:13][O:14][CH2:15][CH2:16][Si:17]([CH3:19])([CH3:18])[CH3:20])[C:9](=[O:21])[CH:8]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 6328Methyl iodideHCID 14798Sodium HydroxideHCID 178481696HCID 178481696, compound

Product 1

HCID 248517054-[4-Methyl-5-(methylthio)-4h-1,2,4-triazol-3-yl]-1-{[2-(trimethylsilyl)ethoxy]methyl}pyridin-2(1h)-oneYield 98%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

The title compound of example 21.1 (21.6 g, 63.8 mmol) was dissolved in a solution of NaOH (5.36 g, 134 mmol) in water (134 mL). When a clear solution was observed, ethanol (40 mL) was added followed by iodomethane (6.37 mL, 102 mmol). The reaction mixture was stirred overnight at room temperature. The reaction mixture was then extracted four times with chloroform and the combined organic layer was dried over sodium sulfate and concentrated to give the title product (22.0 g, 98%).

Workup

  1. extractionThe reaction mixture was then extracted four times with chloroform
  2. dry with materialthe combined organic layer was dried over sodium sulfate
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-52f6b9258add43d9bd9052d34b31e142
Source dataset
uspto-grants-2010_08
Patent number
US07772235B2

Reaction notes

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