Thionyl Chloride → 1-Benzyl-2-chloromethyl-4,5-dimethylimidazole hydrochloride

HRID 65043Notes

Reaction equation

HRID 65043 reaction equation
[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]1[CH2:15]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:19])=O>ClCCl>[ClH:19].[CH2:1]([N:8]1[C:12]([CH3:13])=[C:11]([CH3:14])[N:10]=[C:9]1[CH2:15][Cl:19])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 24386Thionyl ChlorideHCID 202350581-Benzyl-4,5-dimethyl-2-hydroxymethylimidazole

Product 1

HCID 202350701-Benzyl-2-chloromethyl-4,5-dimethylimidazole hydrochloride

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A suspension of 15 g (69 mmol) of 1-benzyl-4,5-dimethyl-2-hydroxymethylimidazole in 50 ml of dichloromethane was added portionwise over a period of 30 minutes to a stirred solution of 25 ml of thionyl chloride in 25 ml of dichloromethane. The solution obtained was boiled under reflux for 1.5 hours and then left to stand at room temperature overnight. Evaporation of the solution gave 23.5 g of crude 1-benzyl-2-chloromethyl-4,5-dimethylimidazole hydrochloride in the form of an oil which was used in the next step without further purification.

Workup

  1. customThe solution obtained
  2. temperatureunder reflux for 1.5 hours
  3. waitleft
  4. customEvaporation of the solution

Sources & evidence

ORD record
ord-3f551307f9ae4dd6afb0266168cd2c7e
Source dataset
uspto-grants-1986_09
Patent number
US04612324

Reaction notes

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