Dimethylformamide → 2-[(2,6-Dichloropyridin-3-yl)oxy]propanoyl chloride

HRID 1995256Notes

Reaction equation

HRID 1995256 reaction equation
[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:13])[C:10](O)=[O:11])=[CH:6][CH:5]=[C:4]([Cl:14])[N:3]=1.CN(C)C=O.S(Cl)([Cl:22])=O>C(Cl)(Cl)Cl>[Cl:1][C:2]1[C:7]([O:8][CH:9]([CH3:13])[C:10]([Cl:22])=[O:11])=[CH:6][CH:5]=[C:4]([Cl:14])[N:3]=1

Participants

5

Reactant 3

HCID 6228DimethylformamideHCID 24386Thionyl ChlorideHCID 129061732-[(2,6-Dichloropyridin-3-yl)oxy]propanoic acid

Product 1

HCID 129061742-[(2,6-Dichloropyridin-3-yl)oxy]propanoyl chloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent2×

Procedure

23.6 g (0.1 mole) of 2-[(2,6-dichloro-3-pyridyl)oxy]propionic acid, 150 ml of chloroform and 1.5 ml of dimethylformamide were heated with stirring at 55°, and an addition was then made dropwise in the course of 1 hour of a solution of 18 g (0.15 mole) of thionyl chloride in 40 ml of chloroform. The reaction mixture was subsequently refluxed for 16 hours and afterwards concentrated in vacuo. The resulting product was used directly for further reactions.

Workup

  1. additionan addition
  2. temperatureThe reaction mixture was subsequently refluxed for 16 hours
  3. concentrationafterwards concentrated in vacuo

Sources & evidence

ORD record
ord-0d83799187bd46c1866ebecc757701c5
Source dataset
uspto-grants-1983_09
Patent number
US04404020

Reaction notes

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