Phosphorus pentachloride → Pyridine-3-sulfonyl chloride
Reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([OH:10])(=O)=[O:8])[CH:2]=1.P(Cl)(Cl)(Cl)(Cl)[Cl:12]>C1(C)C=CC=CC=1.C1C=CC=CC=1>[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([S:7]([Cl:12])(=[O:10])=[O:8])[CH:2]=1Participants
5
Reactant 2
Product 1
Reagents, catalysts & solvents 2
Procedure
3-Pyridylsulfonic acid (30 g, 0.188 mole) was added to PCl5 (46.8 g, 0.225 mole), suspended in 150 mL toluene and heated to reflux overnight. The suspension was cooled and concentrated to yield a yellow oil, which was diluted with benzene, filtered through a pad of celite and concentrated to give 30.7 g (92%) of 23-10 as a yellow oil, which was used in the next step without purification.
Workup
- temperatureheated
- temperatureto reflux overnight
- temperatureThe suspension was cooled
- concentrationconcentrated
- customto yield a yellow oil, which
- filtrationfiltered through a pad of celite
- concentrationconcentrated
Sources & evidence
- ORD record
- ord-bf556213779245328caa8e5257c096ab
- Source dataset
- uspto-grants-1995_05
- Patent number
- US05416099
Reaction notes
Loading…