Thionyl Chloride → 2-Chloromethyl-1-propylimidazole hydrochloride

HRID 856753Notes

Reaction equation

HRID 856753 reaction equation
O[CH2:2][C:3]1[N:4]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:6][N:7]=1.S(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][CH2:2][C:3]1[N:4]([CH2:8][CH2:9][CH3:10])[CH:5]=[CH:6][N:7]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 557333(1-Propyl-1H-imidazol-2-yl)methanol

Product 1

HCID 229384382-Chloromethyl-1-propylimidazole hydrochloride

Conditions

Temperature
90 °C

Procedure

To 2-hydroxymethyl-1-propylimidazole (8.0 g) was added thionyl chloride (50 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 methanol-ethyl acetate, to give 2-chloromethyl-1-propylimidazole hydrochloride (4.3 g) as yellow crystals.

Workup

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

Sources & evidence

ORD record
ord-06c3e0b73d594c86b1f4ba5aa1414ce9
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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