Thionyl Chloride → 2-Chloromethyl-3-ethoxypyridine hydrochloride

HRID 263241

Reaction equation

HRID 263241 reaction equation
S(Cl)([Cl:3])=O.[CH2:5]([O:7][C:8]1[C:9]([CH2:14]O)=[N:10][CH:11]=[CH:12][CH:13]=1)[CH3:6]>C(Cl)(Cl)Cl>[ClH:3].[Cl:3][CH2:14][C:9]1[C:8]([O:7][CH2:5][CH3:6])=[CH:13][CH:12]=[CH:11][N:10]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 22018715(3-Ethoxypyridin-2-yl)methanol

Product 1

HCID 204741852-Chloromethyl-3-ethoxypyridine hydrochloride

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

Thionyl chloride (8 cc) was added over 8 minutes to a stirred solution of 3-ethoxy-2-hydroxymethylpyridine (5.6 g) in chloroform (60 cc) at room temperature. After 11/2 hrs the mixture was evaporated to dryness and the residue was recrystallised from 0.16 M ethanolic hydrogen chloride/diethyl ether (1:1) to give 2-chloromethyl-3-ethoxypyridine hydrochloride (6.5 g) m.p. 176°-179.5°. (decomp.).

Workup

  1. customAfter 11/2 hrs the mixture was evaporated to dryness
  2. customthe residue was recrystallised from 0.16 M ethanolic hydrogen chloride/diethyl ether (1:1)

Sources & evidence

ORD record
ord-0572a0990f034a81beadd8005107c15c
Source dataset
uspto-grants-1979_05
Patent number
US04156727

Linked notes

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