Thionyl Chloride → 1-chloro-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane

HRID 54514Notes

Reaction equation

HRID 54514 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH:8](O)[CH2:9][N:10]2[CH:14]=[CH:13][N:12]=[CH:11]2)=[N:6][CH:7]=1.S(Cl)([Cl:18])=O>C1(C)C=CC=CC=1>[Cl:18][CH:8]([C:5]1[CH:4]=[CH:3][C:2]([Cl:1])=[CH:7][N:6]=1)[CH2:9][N:10]1[CH:14]=[CH:13][N:12]=[CH:11]1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 199594181-(5-Chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane-1-ol

Product 1

HCID 199594231-chloro-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

1 g of 1-(5-chloro-2-pyridyl)-2-(1H-imidazol-1-yl)ethane-1-ol is dissolved in 2 ml of toluene, 6 ml of thionyl chloride are added and the reaction mixture is stirred for 30 minutes at room temperature. The solvent and the thionyl chloride in excess are distilled off, the residue is dissolved in 2N NaOH, extracted with ethyl acetate, dried over Na2SO4 and evaporated to yield the compound as a colourless oil.

Workup

  1. distillationThe solvent and the thionyl chloride in excess are distilled off
  2. dissolutionthe residue is dissolved in 2N NaOH
  3. extractionextracted with ethyl acetate
  4. dry with materialdried over Na2SO4
  5. customevaporated

Sources & evidence

ORD record
ord-3294db1eb1ce4e988dd4e58e736a0c00
Source dataset
uspto-grants-1997_04
Patent number
US05622982

Reaction notes

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