Thionyl Chloride → 2-Chloro-5-chloromethylpyridine hydrochloride

HRID 1585004Notes

Reaction equation

HRID 1585004 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-452971cbae434669b31e1fcc55c5da8f
Source dataset
uspto-grants-1999_08
Patent number
US05935981

Reaction notes

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