Thionyl Chloride → 2-Chloromethyl-1-propylimidazole hydrochloride

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

Reactant 2

HCID 24386Thionyl Chloride

HCID 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

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

Sources & evidence

ORD record: ord-06c3e0b73d594c86b1f4ba5aa1414ce9
Source dataset: uspto-grants-2007_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07262185B2

Reaction notes

Loading…