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

HRID 1267620Notes

Reaction equation

HRID 1267620 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 a saturated aqueous solution of sodium hydrogencarbonate and saturated brine, dried over anhydrous sodium sulfate and concentrated under reduced pressure. The residue was then recrystallized from chloroform-hexane to obtain the title compound.

Workup

  1. washThe reaction mixture was washed with a saturated aqueous solution of sodium hydrogencarbonate and saturated brine
  2. dry with materialdried over anhydrous sodium sulfate
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was then recrystallized from chloroform-hexane

Sources & evidence

ORD record
ord-12aea223db204d2f861970bcd9d981bf
Source dataset
uspto-grants-2003_04
Patent number
US06552188B2

Reaction notes

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