Thionyl Chloride → (+/-)-2-(1-Chloroethyl)-6-methylpyridine hydrochloride

HRID 911433

Reaction equation

HRID 911433 reaction equation
O[CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]=1)[CH3:3].S(Cl)([Cl:13])=O>C(Cl)Cl>[ClH:13].[Cl:13][CH:2]([C:4]1[CH:9]=[CH:8][CH:7]=[C:6]([CH3:10])[N:5]=1)[CH3:3]

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 3531381-(6-Methylpyridin-2-yl)ethanol

Product 1

HCID 66706611(+/-)-2-(1-Chloroethyl)-6-methylpyridine hydrochlorideYield 85%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To the crude 2-(1-hydroxyethyl)-6-methylpyridine (1.6 g, 11.7 mmol) in dry DCM (15 mL) add with stirring thionyl chloride (2.0 mL, 27 mmol) and continue stirring overnight Concentrate in vacuo, azeotrope three times with dry chloroform and dry under high vacuum to provide the title compound as a tan solid (1.9 g, 85%). MS (APCI+) m/z 156 (M+H)+.

Workup

  1. concentrationConcentrate in vacuo
  2. customdry under high vacuum

Sources & evidence

ORD record
ord-a65254b7cd5c4aea8e7be1512f5c8d13
Source dataset
uspto-grants-2011_09
Patent number
US08022062B2

Linked notes

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