Thionyl Chloride → 5-Chloromethyl-4-methyl-1-propylimidazole hydrochloride

HRID 856778Notes

Reaction equation

HRID 856778 reaction equation
O[CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][C:4]=1[CH3:11].S(Cl)([Cl:14])=O>>[ClH:14].[Cl:14][CH2:2][C:3]1[N:7]([CH2:8][CH2:9][CH3:10])[CH:6]=[N:5][C:4]=1[CH3:11]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 229387645-Hydroxymethyl-4-methyl-1-propylimidazole

Product 1

HCID 229385505-Chloromethyl-4-methyl-1-propylimidazole hydrochloride

Conditions

Temperature
90 °C

Procedure

To 5-hydroxymethyl-4-methyl-1-propylimidazole (2.4 g) was added thionyl chloride (10 ml) at 0° C., and the mixture was heated for 30 minutes 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. The solvent was distilled off again under reduced pressure, to give 5-chloromethyl-4-methyl-1-propylimidazole hydrochloride (3.13 g) as brown oil.

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

Sources & evidence

ORD record
ord-3112afcb917c407aa31fbe834092ed52
Source dataset
uspto-grants-2007_08
Patent number
US07262185B2

Reaction notes

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