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

HRID 1004613Notes

Reaction equation

HRID 1004613 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-7d0b339719e04be6aaa36ccc1a6d96a9
Source dataset
uspto-grants-2000_04
Patent number
US06051574

Reaction notes

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