Thionyl Chloride → (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride

HRID 569146Notes

Reaction equation

HRID 569146 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[CH2:16]O)=[CH:10][CH:9]=2)[CH:2]=1.S(Cl)([Cl:20])=O>C(Cl)Cl>[ClH:20].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[CH:15]/[CH2:16][Cl:20])=[CH:10][CH:9]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 15594566(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl alcohol

Product 1

HCID 14099894(E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 100 ml of methylene chloride was dissolved 10.5 g of (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl alcohol, and 17 ml of thionyl chloride was added dropwise to the resulting solution with ice-cooling, after which the resulting mixture was subjected to reaction under reflux for 30 minutes. The solvent and the excessive thionyl chloride were removed by distillation under reduced pressure, to obtain (E)-3-[4-(pyridin-3-ylmethyl)phenyl]allyl chloride hydrochloride as the residue. This residue was dissolved in 40 ml of dimethyl sulfoxide.

Workup

  1. additionwas added dropwise to the resulting solution with ice-
  2. temperaturecooling
  3. customafter which the resulting mixture was subjected to reaction
  4. temperatureunder reflux for 30 minutes
  5. customThe solvent and the excessive thionyl chloride were removed by distillation under reduced pressure

Sources & evidence

ORD record
ord-c1c60f60c303418e984f1ffc34df4d5a
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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