Thionyl Chloride → 5-(chloromethyl)-1-propyl-1H-imidazole hydrochloride

HRID 856769Notes

Reaction equation

HRID 856769 reaction equation
O[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][CH:4]=1.S(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22938539(1-propyl-1H-imidazol-5-yl)methanol

Product 1

HCID 229386165-(chloromethyl)-1-propyl-1H-imidazole hydrochloride

Conditions

Temperature
90 °C

Procedure

To 5-hydroxymethyl-1-propylimidazole (33.0 g) was added by portions thionyl chloride (80 ml) at 0° C., and the mixture was heated for 30 minutes under nitrogen atmosphere at 90° C. The mixture was allowed to be at room temperature. The solvent was distilled off under reduced pressure and the obtained residue was dissolved in methanol, and the solvent was distilled off again under reduced pressure. The obtained solid was recrystallized from ethyl acetate, to give 5-chloromethyl-1-propylimidazole hydrochloride (43.8 g) as colorless crystals.

Workup

  1. customto be at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. dissolutionthe obtained residue was dissolved in methanol
  4. distillationthe solvent was distilled off again under reduced pressure
  5. customThe obtained solid was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-b44bb6b4a29f40c796ce685311e85702
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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