Thionyl Chloride → 3-Pyridin-3-ylpropanoyl chloride

HRID 613239Notes

Reaction equation

HRID 613239 reaction equation
S(Cl)([Cl:3])=O.[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][C:13]([OH:15])=O)[CH:6]=1>[Cl-].C([N+](CC)(CC)CC)C1C=CC=CC=1.ClCCCl>[N:5]1[CH:10]=[CH:9][CH:8]=[C:7]([CH2:11][CH2:12][C:13]([Cl:3])=[O:15])[CH:6]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 2596243-(Pyridin-3-yl)propanoic acid

Product 1

HCID 149870663-Pyridin-3-ylpropanoyl chloride

Reagents, catalysts & solvents 2

HCID 66133Benzyl triethylammonium chlorideCatalystHCID 111,2-DichloroethaneSolvent

Procedure

Add thionyl chloride (0.05 mL, 0.53 mmol) to a stirred suspension of 3-(3-pyridyl)propionic acid (80.2 mg, 0.53 mmol) and benzyltriethylammonium chloride (1 mg, 0.004 mmol) in 1,2-dichloroethane (20 mL) and heat to reflux for 2.5 hours. Cool the reaction mixture to room temperature and concentrate in vacuo. Azeotrope the residue with CCl4 and place under vacuum. Use the resulting acid chloride without further purification.

Workup

  1. temperatureheat
  2. temperatureto reflux for 2.5 hours
  3. concentrationconcentrate in vacuo
  4. customwithout further purification

Sources & evidence

ORD record
ord-da6f477ca9344f2ab17f08116fd10489
Source dataset
uspto-grants-1999_12
Patent number
US06008196

Reaction notes

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