Methyl iodide → 1-Butyl-3-hydroxy-4-methylpyridine-2-thione
Reaction equation
[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([CH2:11]N(C)C)=[C:7]([OH:15])[C:6]1=[S:16])[CH2:2][CH2:3][CH3:4].IC>C(Cl)Cl>[CH2:1]([N:5]1[CH:10]=[CH:9][C:8]([CH3:11])=[C:7]([OH:15])[C:6]1=[S:16])[CH2:2][CH2:3][CH3:4]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
To a solution of 1-butyl-3-hydroxy-4(N,N-dimethylaminomethyl)pyridine-2-thione (2-034-05) (1.0 g) in methylene chloride (20 mL) was added iodomethane (2.1 g) at room temperature. After the reaction mixture was stirred for 1 h, the solvent was evaporated under reduced pressure. To the residue were added ethanol (20 mL) and triphenylphosphine (1.6 g), and the reaction mixture was stirred at 75° C. for 20 h, and evaporated under reduced pressure. To the residue were added methanol (10 mL) and 1 mol/L aqueous sodium hydroxide solution (8 mL), and the reaction mixture was stirred at 60° C. for 2 h, and evaporated under reduced pressure. The crude product was purified by silica gel column chromatography (toluene/acetone=4/1) to give 1-butyl-3-hydroxy-4-methylpyridine-2-thione (2-034-06) (0.57 g, 70%) as an oil.