Thionyl Chloride → HCID 20148646, compound

HRID 569181Notes

Reaction equation

HRID 569181 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]=[C:15](\[CH3:18])/[CH2:16]O)=[CH:10][CH:9]=2)[CH:2]=1.S(Cl)([Cl:21])=O>C(Cl)Cl>[ClH:21].[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([CH2:7][C:8]2[CH:13]=[CH:12][C:11](/[CH:14]=[C:15](\[CH3:18])/[CH2:16][Cl:21])=[CH:10][CH:9]=2)[CH:2]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 13745530HCID 13745530, compound

Product 1

HCID 20148646HCID 20148646, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 24 ml of methylene chloride was dissolved 1.2 g of (E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl alcohol, and 1.8 ml of thionyl chloride was dropped into 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 as the residue (E)-3-[4-(pyridin-3-ylmethyl)phenyl]-2-methylallyl chloride hydrochloride. This was crystallized from a mixed solvent of 2-propanol and ethyl acetate to obtain colorless, needle-like crystals having a melting point of 118°-120° C.

Workup

  1. additionwas dropped into 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-9cb5a9aef8cf4958ab58326092272195
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

Loading…