Thionyl Chloride → 3-(2-Pyridinyloxy)benzoyl chloride

HRID 1579004Notes

Reaction equation

HRID 1579004 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11](O)=[O:12].S(Cl)([Cl:19])=O>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[O:7][C:8]1[CH:9]=[C:10]([CH:14]=[CH:15][CH:16]=1)[C:11]([Cl:19])=[O:12]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 219014233-[(Pyridin-2-yl)oxy]benzoic acid

Product 1

HCID 130348853-(2-Pyridinyloxy)benzoyl chloride

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a suspension of 3-(2-pyridyloxy)benzoic acid (1.80 g) in thionyl chloride (5.4 ml), dimethylformamide (0.2 ml is added, and the resultant mixture is stirred at room temperature for 2.5 hours. The reaction mixture is evaporated under reduced pressure to remove the excessive thionyl chloride, and the residue is combined with anhydrous pyridine (0.73 g) and anhydrous benzene (40 ml). The precipitated pyridine hydrochloride is filtered off. The filtrate is evaporated to remove the benzene, and the residue is dissolved in anhydrous ether (20 ml). The ether solution is filtered to remove the insoluble substance. The filtrate is evaporated to remove the ether, whereby 3-(2-pyridyloxy)benzoyl chloride is obtained. IR (CCl4): 1774 cm-1.

Workup

  1. additionis added
  2. customThe reaction mixture is evaporated under reduced pressure
  3. customto remove the excessive thionyl chloride
  4. filtrationThe precipitated pyridine hydrochloride is filtered off
  5. customThe filtrate is evaporated
  6. customto remove the benzene
  7. dissolutionthe residue is dissolved in anhydrous ether (20 ml)
  8. filtrationThe ether solution is filtered
  9. customto remove the insoluble substance
  10. customThe filtrate is evaporated
  11. customto remove the ether

Sources & evidence

ORD record
ord-e20359139ca34228b91261a9c80752ae
Source dataset
uspto-grants-1976_02
Patent number
US03940403

Reaction notes

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