Thionyl Chloride → 4-chloro-2-(chloromethyl)-3-methoxypyridine

HRID 1793651Notes

Reaction equation

HRID 1793651 reaction equation
Cl.O[CH2:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([Cl:12])[CH:7]=[CH:6][N:5]=1.S(Cl)([Cl:15])=O>C1(C)C=CC=CC=1>[Cl:15][CH2:3][C:4]1[C:9]([O:10][CH3:11])=[C:8]([Cl:12])[CH:7]=[CH:6][N:5]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22022897HCID 22022897, compound

Product 1

HCID 118163554-chloro-2-(chloromethyl)-3-methoxypyridine

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A 1000 ml round-bottom flask is loaded with 67 g (0.319 mol) of 2-hydroxymethyl-3-methoxy-4-chloro-pyridine hydrochloride and 469 ml of toluene. 73 g (0.606 mol) of thionyl chloride are then dropped therein, under stirring and at inner temperature of about 15–25° C. After completion of the addition, the mixture is washed with 35 ml of toluene, keeping the suspension at this temperature for at least 1 hour. After completion of the reaction, approx. 200 ml of solvent are distilled off under vacuum. The suspension, containing 2-chloromethyl-3-methoxy-4-chloro-pyridine, is then subjected to the subsequent step.

Workup

  1. additionAfter completion of the addition
  2. washthe mixture is washed with 35 ml of toluene
  3. customfor at least 1 hour
  4. customAfter completion of the reaction, approx. 200 ml of solvent
  5. distillationare distilled off under vacuum
  6. additionThe suspension, containing 2-chloromethyl-3-methoxy-4-chloro-pyridine

Sources & evidence

ORD record
ord-6e0d738309634983917a5ab5ec75e95e
Source dataset
uspto-grants-2006_07
Patent number
US07081534B2

Reaction notes

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