Thionyl Chloride → HCID 20148610, compound

HRID 569171Notes

Reaction equation

HRID 569171 reaction equation
[ClH:1].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH3:19])/[CH2:17]O)=[CH:11][CH:10]=2)[CH:3]=1.S(Cl)([Cl:22])=O>C(Cl)Cl>[ClH:22].[N:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][C:9]2[CH:14]=[CH:13][C:12](/[CH:15]=[C:16](\[CH3:19])/[CH2:17][Cl:1])=[CH:11][CH:10]=2)[CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 70414624HCID 70414624, compound

Product 1

HCID 20148610HCID 20148610, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

In 5 ml of methylene chloride was suspended 350 mg of (E)-3-[4-(pyridin-3-yloxy)phenyl]-2-methylallyl alcohol hydrochloride and to the suspension was added 0.18 ml of thionyl chloride 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 oily (E)-3-[4-(pyridin-3-yloxy)phenyl]-2-methylallyl chloride hydrochloride. This was dissolved in 2 ml of methylene chloride.

Workup

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

Sources & evidence

ORD record
ord-655c5f845b464f0c8ce2d94d609581b5
Source dataset
uspto-grants-1988_03
Patent number
US04731370

Reaction notes

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