Thionyl Chloride → 2-(Chloromethyl)-6-isopropylpyridine hydrochloride

HRID 706725Notes

Reaction equation

HRID 706725 reaction equation
[CH:1]([C:4]1[N:9]=[C:8]([CH2:10]O)[CH:7]=[CH:6][CH:5]=1)([CH3:3])[CH3:2].S(Cl)([Cl:14])=O>C(Cl)Cl>[ClH:14].[Cl:14][CH2:10][C:8]1[CH:7]=[CH:6][CH:5]=[C:4]([CH:1]([CH3:3])[CH3:2])[N:9]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 21874757(6-(Propan-2-yl)pyridin-2-yl)methanol

Product 1

HCID 679741532-(Chloromethyl)-6-isopropylpyridine hydrochlorideYield 98%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To (6-isopropylpyridin-2-yl)methanol (3.13 g, 20.7 mmol) in DCM (20 mL) at 0° C. was added sulfurous dichloride (12.3 g, 104 mmol). The cold bath was removed and the reaction mixture was stirred for one hour. Solvent was removed under reduced pressure to give the desired product (98%).

Workup

  1. customThe cold bath was removed
  2. customSolvent was removed under reduced pressure

Sources & evidence

ORD record
ord-d6370ff8f8484258ac906857b636383c
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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