Thionyl Chloride → 1-(4-Cyanobenzyl)-5-chloromethyl-2-methylimidazole hydrochloride salt

HRID 1068441Notes

Reaction equation

HRID 1068441 reaction equation
[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([CH2:13]O)=[CH:11][N:10]=[C:9]2[CH3:15])=[CH:5][CH:4]=1)#[N:2].S(Cl)([Cl:20])=O>>[ClH:20].[C:1]([C:3]1[CH:17]=[CH:16][C:6]([CH2:7][N:8]2[C:12]([CH2:13][Cl:20])=[CH:11][N:10]=[C:9]2[CH3:15])=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 211934151-(4-Cyanobenzyl)-5-hydroxymethyl-2-methylimidazole

Product 1

HCID 211933481-(4-Cyanobenzyl)-5-chloromethyl-2-methylimidazole hydrochloride salt

Procedure

A mixture of 1-(4-cyanobenzyl)-5-hydroxymethyl-2-methylimidazole (3.45 g, 15.2 mmol) and thionyl chloride (30 mL, 411 mmol) was stirred at room temp. overnight under a calcium chloride drying tube. The resultant mixture was concentrated under vacuum, and residual thionyl chloride was removed by co-evaporation with toluene. The residue was triturated with anhydrous diethyl ether, filtered, washed with ether to provide the title compound as white solid.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum, and residual thionyl chloride
  2. customwas removed by co-evaporation with toluene
  3. customThe residue was triturated with anhydrous diethyl ether
  4. filtrationfiltered
  5. washwashed with ether

Sources & evidence

ORD record
ord-4ac8f2a410e64afbb3e389b1be355637
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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