Thionyl Chloride → Pyridine, 3-(2-chloroethyl)-, hydrochloride

HRID 1682192Notes

Reaction equation

HRID 1682192 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8]O)[CH:2]=1.S(Cl)([Cl:12])=O>C(Cl)(Cl)Cl>[ClH:12].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][CH2:8][Cl:12])[CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 805153-Pyridineethanol

Product 1

HCID 199465Pyridine, 3-(2-chloroethyl)-, hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

In 100 ml of CHCl3 was dissolved 6.39 g (0.052 mole) of 2-(3-pyridyl)ethanol followed by dropwise addition of 15.6 ml of thionyl chloride with stirring at room temperature. Then, the mixture was stirred for 1.5 hours, after which the solvent was distilled off. After addition of ether, crystals were recovered by filtration and dried. The procedure gave 9.13 g of 2-(3-pyridyl)ethyl chloride hydrochloride as white crystals.

Workup

  1. stirringThen, the mixture was stirred for 1.5 hours
  2. distillationafter which the solvent was distilled off
  3. additionAfter addition of ether, crystals
  4. filtrationwere recovered by filtration
  5. customdried

Sources & evidence

ORD record
ord-3e76cddc8e85419a9c747f78005483e2
Source dataset
uspto-grants-1992_12
Patent number
US05175301

Reaction notes

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