Thionyl Chloride → 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride

HRID 856761

Reaction equation

HRID 856761 reaction equation
O[CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.S(Cl)([Cl:11])=O>>[ClH:11].[Cl:11][CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 573612(1-methyl-1H-imidazol-2-yl)methanol

Product 1

HCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochloride

Conditions

Temperature
90 °C

Procedure

To 2-hydroxymethyl-1-methylimidazole (874 mg) was added thionyl chloride (10 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 recrystallized from ethyl acetate, to give 2-chloromethyl-1-methylimidazole hydrochloride (1.15 g) as brown crystals.

Workup

  1. customto be at room temperature
  2. distillationThe solvent was distilled off under reduced pressure
  3. customthe obtained residue was recrystallized from ethyl acetate

Sources & evidence

ORD record
ord-55507ce07af64445b0909f7af6bd6c7e
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Linked notes

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