Thionyl Chloride → 1-(4-Cyanobenzyl)-5-(chloromethyl)imidazole

HRID 342704Notes

Reaction equation

HRID 342704 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>>[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 97953581-(4-Cyanobenzyl)-5-(chloromethyl)imidazole

Procedure

A solution of 1-(4-cyanobenzyl)-5-(hydroxymethyl)imidazole (1.00 g, 4.70 mmol), in thionyl chloride (5 mL), was stirred at 70° C. for 16 hours. The solvent was evaporated in vacuo and the resulting solid suspended in CH2Cl2, collected by filtration and dried in vacuo. The material was sufficiently pure for use in the next step without further purification.

Workup

  1. customThe solvent was evaporated in vacuo
  2. filtrationcollected by filtration
  3. customdried in vacuo
  4. customThe material was sufficiently pure for use in the next step without further purification

Sources & evidence

ORD record
ord-ac8df5ad80a34bc6bc9fed1ecd1e9d12
Source dataset
uspto-grants-1999_01
Patent number
US05859035

Reaction notes

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