Thionyl Chloride → 4-chloropyridine-2-carbonyl Chloride
Reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([OH:10])=O)[CH:3]=1.S(Cl)([Cl:13])=O>ClC(Cl)C.CN(C=O)C>[Cl:1][C:2]1[CH:7]=[CH:6][N:5]=[C:4]([C:8]([Cl:13])=[O:10])[CH:3]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 85 °C
Procedure
To a suspension of 4-chloro-pyridine-2-carboxylic acid (2.0 g, 12.8 mmol) in dichloroethane (43 mL) was added thionyl chloride (2.8 mL, 38.5 mmol) and DMF (2-3 drops). The suspension was warmed to 85° C. After 1 h, the resulting clear, yellow solution was cooled to rt and concentrated. The residue was dissolved in DCE and concentrated. This process was repeated two additional times to give a yellow liquid which crystallized upon standing to give a yellow solid.
Workup
- temperaturethe resulting clear, yellow solution was cooled to rt
- concentrationconcentrated
- dissolutionThe residue was dissolved in DCE
- concentrationconcentrated
- customto give a yellow liquid which
- customcrystallized
- customto give a yellow solid
Sources & evidence
- ORD record
- ord-e1050bfdd97b47468527223b3b408c37
- Source dataset
- uspto-grants-2015_07
- Patent number
- US09079918B2
Reaction notes
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