Thionyl Chloride → 2-Chloro-5-chloromethylpyridine hydrochloride

HRID 249484Notes

Reaction equation

HRID 249484 reaction equation
[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8]O)=[CH:4][CH:3]=1.S(Cl)([Cl:12])=O>C(Cl)(Cl)Cl.CCOCC>[ClH:1].[Cl:1][C:2]1[N:7]=[CH:6][C:5]([CH2:8][Cl:12])=[CH:4][CH:3]=1

Participants

5

Reactant 2

HCID 24386Thionyl ChlorideHCID 177161(6-Chloropyridin-3-yl)methanol

Product 1

HCID 224503272-Chloro-5-chloromethylpyridine hydrochloride

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6212ChloroformSolvent

Procedure

In 500 ml of CHCl3 was dissolved 47.3 g (0.33 mole) of 6-chloro-3-pyridylmethanol followed by dropwise addition of 99.3 ml of thionyl chloride with stirring at room temperature. After completion of the dropwise addition, the mixture was further stirred for 1.5 hours and, then, allowed to stand overnight. The CHCl3 was distilled off under reduced pressure, whereby crystals and oil were obtained as a residue. The residue was diluted with ether, collected by filtration and dried to give 45.2 g of 6-chloro-3-pyridylmethyl chloride hydrochloride as white crystals.

Workup

  1. additionAfter completion of the dropwise addition
  2. stirringthe mixture was further stirred for 1.5 hours
  3. distillationThe CHCl3 was distilled off under reduced pressure, whereby crystals
  4. customoil were obtained as a residue
  5. filtrationcollected by filtration
  6. customdried

Sources & evidence

ORD record
ord-fc73b76b5b754717952b85f0f2a4cd82
Source dataset
uspto-grants-1993_05
Patent number
US05214152

Reaction notes

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