Thionyl Chloride → 4-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

HRID 1422356Notes

Reaction equation

HRID 1422356 reaction equation
[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13]O)=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2].S(Cl)([Cl:19])=O>>[ClH:19].[C:1]([C:3]1[CH:16]=[CH:15][C:6]([CH2:7][N:8]2[C:12]([CH2:13][Cl:19])=[CH:11][N:10]=[CH:9]2)=[CH:5][CH:4]=1)#[N:2]

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 101982471-(4-Cyanobenzyl)-5-hydroxymethyl-1H-imidazole

Product 1

HCID 97953574-((5-(Chloromethyl)-1H-imidazol-1-yl)methyl)benzonitrile hydrochloride

Conditions

Temperature
60 °C

Procedure

A suspension of 1-(4-cyanobenzyl)-5-hydroxymethylimidazole (Example 26, step D; 3.1 g, 14.5 mmol) in thionyl chloride (20 mL) was heated at 60° C. for 18 h. The excess thionyl chloride was removed in vacuo and the residue was azeotroped with CHCl3 (3×) to give the title compound.

Workup

  1. customThe excess thionyl chloride was removed in vacuo
  2. customthe residue was azeotroped with CHCl3 (3×)

Sources & evidence

ORD record
ord-e7fb3e7c1d11470aa974f46bf4f7d735
Source dataset
uspto-grants-2000_06
Patent number
US06080870

Reaction notes

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