Thionyl Chloride → HCID 22938531, compound

HRID 856775Notes

Reaction equation

HRID 856775 reaction equation
O[CH2:2][C:3]1[N:7]([CH:8]([CH3:10])[CH3:9])[CH:6]=[N:5][CH:4]=1.S(Cl)([Cl:13])=O>>[ClH:13].[Cl:13][CH2:2][C:3]1[N:7]([CH:8]([CH3:10])[CH3:9])[CH:6]=[N:5][CH:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 20568531(1-(propan-2-yl)-1H-imidazol-5-yl)methanol

Product 1

HCID 22938531HCID 22938531, compound

Conditions

Temperature
90 °C

Procedure

To 5-hydroxymethyl-1-isopropylimidazole (4.5 g), thionyl chloride (20 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-isopropylimidazole hydrochloride (6.2 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-22215d6b82654220bea74dff3256e168
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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