Toluene → 2-Chloromethyl-4,5-dimethoxypyridinium chloride
Reaction equation
S(Cl)([Cl:3])=O.O[CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][N:8]=1.C1(C)C=CC=CC=1>C(Cl)Cl>[Cl-:3].[Cl:3][CH2:6][C:7]1[CH:12]=[C:11]([O:13][CH3:14])[C:10]([O:15][CH3:16])=[CH:9][NH+:8]=1Participants
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 20 °C
Procedure
3 ml of thionyl chloride, dissolved in 10 ml of methylene chloride, are added dropwise to a solution, cooled to 0° C., of 5 g of 2-hydroxymethyl-4,5-dimethoxypyridine in 40 ml of methylene chloride in the course of one hour, the reaction mixture is then stirred at 20° C. for 4 hours, during which it becomes red-colored, 5 ml of toluene are added and the mixture is concentrated completely on a rotary evaporator (30° C./5 mbar). The oily residue is dissolved in 50 ml of warm isopropanol and the solution is clarified with a little Tonsil®, filtered and concentrated again. The residue is taken up in 10 ml of toluene and the solution is made to crystallize with petroleum ether. After cooling in an ice-bath, the precipitate is filtered off with suction, washed with petroleum ether and dried. 4.6 g (70% of theory) of the title compound 2-chloromethyl-4,5-dimethoxy-pyridinium chloride are obtained as a colourless soldi; decomp. at 160°- 61° C.
Workup
- additionare added dropwise to a solution
- concentrationthe mixture is concentrated completely on a rotary evaporator (30° C./5 mbar)
- dissolutionThe oily residue is dissolved in 50 ml of warm isopropanol
- filtrationfiltered
- concentrationconcentrated again
- customto crystallize with petroleum ether
- temperatureAfter cooling in an ice-bath
- filtrationthe precipitate is filtered off with suction
- washwashed with petroleum ether
- customdried
Sources & evidence
- ORD record
- ord-d101888eeef84d72bb71fed974de176a
- Source dataset
- uspto-grants-1987_08
- Patent number
- US04686230
Reaction notes
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