Thionyl Chloride → 3-Pyridin-3-ylpropanoyl chloride
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]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
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
- temperatureheat
- temperatureto reflux for 2.5 hours
- concentrationconcentrate in vacuo
- customwithout further purification
Sources & evidence
- ORD record
- ord-da6f477ca9344f2ab17f08116fd10489
- Source dataset
- uspto-grants-1999_12
- Patent number
- US06008196
Reaction notes
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