Thionyl Chloride → 4-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

HRID 2303349Notes

Reaction equation

HRID 2303349 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1.S(Cl)([Cl:23])=O>C(Cl)(Cl)Cl>[Cl:23][CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]2[CH:14]=[C:13]([O:15][CH3:16])[C:12]([O:17][CH3:18])=[C:11]([O:19][CH3:20])[CH:10]=2)[CH:4]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 161259364-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine

Product 1

HCID 120192374-Chloromethyl-2-(3,4,5-trimethoxyphenyl) pyridine

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

4-Hydroxymethyl-2-(3,4,5-trimethoxyphenyl)pyridine (18.15 g) was dissolved in chloroform (300 mL) , and to the solution thionyl chloride (19.2 mL) was added at 0° C.. After 30 minutes, the mixture was warmed to room temperature and stirred for 4 hours. The reaction mixture was washed with water and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The resultant crystals were then recrystallized from chloroform-hexane to obtain the title compound.

Workup

  1. washThe reaction mixture was washed with water and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe resultant crystals were then recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-f638af03b64e44049375eef9ca90229e
Source dataset
uspto-grants-2002_08
Patent number
US06432957B1

Reaction notes

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