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

HRID 1833830Notes

Reaction equation

HRID 1833830 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 are heated with stirring to 55°, and in the course of 1 hour a solution of 18 g (0.15 mole) of thionyl chloride in 40 ml of chloroform is added dropwise. The reaction mixture is subsequently refluxed for 16 hours and is afterwards concentrated in vacuo. The product obtained is used directly for further reactions.

Workup

  1. temperatureThe reaction mixture is subsequently refluxed for 16 hours
  2. concentrationis afterwards concentrated in vacuo
  3. customThe product obtained

Sources & evidence

ORD record
ord-44bb6621ad28421f8c8cf23cd617d584
Source dataset
uspto-grants-1978_01
Patent number
US04067725

Reaction notes

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