Thionyl Chloride → 3-(2-Chloroethyl)pyridine

HRID 2049842Notes

Reaction equation

HRID 2049842 reaction equation
O[CH2:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1.S(Cl)([Cl:12])=O>>[Cl:12][CH2:2][CH2:3][C:4]1[CH:5]=[N:6][CH:7]=[CH:8][CH:9]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 805153-Pyridineethanol

Product 1

HCID 1994663-(2-Chloroethyl)pyridine

Procedure

A mixture of 3-(2-hydroxyethyl)pyridine (1.2 g., 9.8 m.moles ) and thionyl chloride (10 ml.) was refluxed for 3 hours and then excess of the thionyl chloride was removed by evaporation. To the residue was added a 5% aqueous solution of Na2CO3 (20 ml.) and the mixture was extracted with chloroform (2×30 ml.). The extracts were combined, dried with anhydrous Na2SO4 and concentrated to dryness to yield 3-(2-chloroethyl)-pyridine, 1.3 g. (98%).

Workup

  1. temperaturewas refluxed for 3 hours
  2. customexcess of the thionyl chloride was removed by evaporation
  3. additionTo the residue was added a 5% aqueous solution of Na2CO3 (20 ml.)
  4. extractionthe mixture was extracted with chloroform (2×30 ml.)
  5. dry with materialdried with anhydrous Na2SO4
  6. concentrationconcentrated to dryness

Sources & evidence

ORD record
ord-c17a55155129400797577a25b7d60172
Source dataset
uspto-grants-1980_04
Patent number
US04198504

Reaction notes

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