Thionyl Chloride → 2-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochloride

HRID 1593228Notes

Reaction equation

HRID 1593228 reaction equation
[CH3:1][O:2][C:3]1[C:8]([CH3:9])=[CH:7][N:6]=[C:5]([CH2:10]O)[C:4]=1[CH3:12].S(Cl)([Cl:15])=O>ClCCl>[ClH:15].[Cl:15][CH2:10][C:5]1[C:4]([CH3:12])=[C:3]([O:2][CH3:1])[C:8]([CH3:9])=[CH:7][N:6]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 7378233,5-Dimethyl-2-hydroxymethyl-4-methoxy-pyridine

Product 1

HCID 116942582-(Chloromethyl)-3,5-dimethyl-4-methoxypyridine hydrochlorideYield 189.8%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 4-methoxy-3,5-dimethylpyridinemethanol (25.1 g, 0.15 mol) in dichloromethane (400 mL) was added a solution of thionyl chloride (18.8 g, 0.158 mol) in dichloromethane (100 mL) over 30 min at room temperature under argon. After an additional 30 min of stirring at room temperature, the solvent was removed under reduced pressure. The solid residue was suspended in hexanes (200 mL) and filtered. The solid was washed with hexanes (50 mL) and air-dried to give 33.3 g (100%) of the title compound as a white solid.

Workup

  1. customthe solvent was removed under reduced pressure
  2. filtrationfiltered
  3. washThe solid was washed with hexanes (50 mL)
  4. customair-dried

Sources & evidence

ORD record
ord-20555d9a24624fa4a903dfec44296d9a
Source dataset
uspto-grants-2007_11
Patent number
US07294716B2

Reaction notes

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