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

HRID 1418079Notes

Reaction equation

HRID 1418079 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-a8b7044f254e4d019ea9d1cad2a56c06
Source dataset
uspto-grants-1999_03
Patent number
US05880140

Reaction notes

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