2-(2-Hydroxyethyl)pyridine → Pyridine, 2-(2-chloroethyl)-, hydrochloride

HRID 1290843Notes

Reaction equation

HRID 1290843 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.S(Cl)([Cl:12])=O>ClCCCl>[Cl:12][CH2:2][CH2:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][N:5]=1.[ClH:12]

Participants

4

Reactant 2

HCID 76752-(2-Hydroxyethyl)pyridineHCID 24386Thionyl Chloride

Product 1

HCID 199467Pyridine, 2-(2-chloroethyl)-, hydrochlorideYield 99.4%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

2-(2-hydroxyethyl)pyridine (5 g, 41 mmol) was dissolved in 10 mL of 1,2-dichloroethane, and thionyl chloride (9.67 g, 81 mmol) was added slowly at room temperature. The reaction mixture was stirred for one hour at room temperature and was then concentrated at reduced pressure. Methylene chloride (20 mL) was twice added to the concentrated residue and then removed under reduced pressure. The resulting concentrated residue was dried in vacuo to give 7.17 g (98.5%) of 2-(2-chloroethyl) pyridine·hydrochloride as a yellow solid: HRMS: calcd for C7 H8N1Cl1 142.0424, found 142.0400.

Workup

  1. concentrationwas then concentrated at reduced pressure
  2. additionMethylene chloride (20 mL) was twice added to the concentrated residue
  3. customremoved under reduced pressure
  4. customThe resulting concentrated residue was dried in vacuo

Sources & evidence

ORD record
ord-8d05252997a44f9c9ce50616f4f13666
Source dataset
uspto-grants-1998_05
Patent number
US05753660

Reaction notes

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