Thionyl Chloride → 5-(Chloromethyl)-1-Ethyl-1H-Imidazole Hydrochloride

HRID 856771Notes

Reaction equation

HRID 856771 reaction equation
[CH2:1]([N:3]1[C:7]([CH2:8]O)=[CH:6][N:5]=[CH:4]1)[CH3:2].S(Cl)([Cl:12])=O>>[ClH:12].[Cl:12][CH2:8][C:7]1[N:3]([CH2:1][CH3:2])[CH:4]=[N:5][CH:6]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 22988641(1-Ethyl-1H-imidazol-5-yl)methanol

Product 1

HCID 229387405-(Chloromethyl)-1-Ethyl-1H-Imidazole Hydrochloride

Conditions

Temperature
90 °C

Procedure

To 1-ethyl-5-hydroxymethylimidazole (9.5 g), thionyl chloride (50 ml) was added by portions 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-ethylimidazole hydrochloride (12.4 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-230b7f53409948d0b950c5669e97b5db
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

Loading…