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

HRID 443260Notes

Reaction equation

HRID 443260 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-4f703951646f40078e6377885a49bf87
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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