Thionyl Chloride → [(3,5,6-Trichloropyridin-2-yl)oxy]acetyl chloride

HRID 463701Notes

Reaction equation

HRID 463701 reaction equation
[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([OH:14])=O)=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1.S(Cl)([Cl:17])=O>C(Cl)Cl.CN(C)C=O>[Cl:1][C:2]1[C:3]([O:10][CH2:11][C:12]([Cl:17])=[O:14])=[N:4][C:5]([Cl:9])=[C:6]([Cl:8])[CH:7]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 41428Triclopyr

Product 1

HCID 13491111[(3,5,6-Trichloropyridin-2-yl)oxy]acetyl chloride

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

To a stirred slurry of 30 g (0.1237 mole) 3,5,6-trichloro-2-pyridyloxyacetic acid in 500 ml methylene chloride, 1 ml N,N-dimethylformamide was added. Then 16.2 g [10 m' (0.136 mole)] thionyl chloride was added dropwise. The mixture was refluxed 31/2 hours. The solvent was stripped in vacuo to give the 3,5,6-trichloro-2-pyridyloxyacetyl chloride as an oil, which was used in step (b) without further isolation.

Workup

  1. temperatureThe mixture was refluxed 31/2 hours

Sources & evidence

ORD record
ord-c1819414dc1d4110a01c3e9f2e876466
Source dataset
uspto-grants-1985_10
Patent number
US04544661

Reaction notes

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