Thionyl Chloride → HCID 22145673, compound

HRID 398249Notes

Reaction equation

HRID 398249 reaction equation
[Cl:1][C:2]1[N:7]=[C:6]([C:8](O)=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12].S(Cl)([Cl:15])=O>CN(C)C=O.C1C=CC=CC=1>[Cl:1][C:2]1[N:7]=[C:6]([C:8]([Cl:15])=[O:9])[CH:5]=[CH:4][C:3]=1[O:11][CH3:12]

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 74719706-Chloro-5-methoxypicolinic acid

Product 1

HCID 22145673HCID 22145673, compoundYield 151.6%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideCatalystHCID 241BenzeneSolvent

Procedure

A mixture of 6-chloro-5-methoxypicolinic acid (1.5 g, 8.0 mmol), thionyl chloride (5 g, 8.0×5.25 mmol), a catalytic amount (35 mg) of N,N-dimethylformamide and 5 ml of benzene was refluxed for 1 hour. Then, thionyl chloride and benzene were distilled off, and the residue was distributed with water and dichloromethane. A dichloromethane layer was separated and dried with sodium sulfate. The solvent was then distilled off to obtain 1.64 g of 6-chloro-5-methoxypicolinic acid chloride. It was dissolved again in 5 ml of dichloromethane and the resultant solution was added dropwise to a solution of phenol (0.79 g, 8×1.05 mmol) and triethyl amine (0.89 g, 8×1.1 mmol) in 30 ml of dichloromethane under cooling with ice. After conclusion of the addition, the reaction solution was stirred at room temperature for 2 hours, followed by adding water to separate an organic layer. The organic layer was washed with a saturated aqueous solution of sodium hydrogen carbonate and dried with sodium sulfate. The organic solvent was distilled off to obtain a white solid.

Workup

  1. distillationThen, thionyl chloride and benzene were distilled off
  2. customA dichloromethane layer was separated
  3. dry with materialdried with sodium sulfate
  4. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-b49e1e250c6a4031aa100b8a45352941
Source dataset
uspto-grants-2003_08
Patent number
US06610853B1

Reaction notes

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