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

HRID 2041316Notes

Reaction equation

HRID 2041316 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 (1 5 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-73c354a2fcf14f059f6bd583ea85b8f1
Source dataset
uspto-grants-2013_11
Patent number
US08580780B2

Reaction notes

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