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

HRID 565595Notes

Reaction equation

HRID 565595 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

Procedure

A mixture of 1-(4-cyanobenzyl)-5-hydroxymethylimidazole (10.8 g, 50.70 mmol) and thionyl chloride (70 mL, 960 mmol) was stirred at room temp. overnight under a calcium chloride drying tube. The resultant mixture was concentrated under vacuum, and residual thionyl chloride removed by co-evaporation with toluene. The residue was recrystallized from boiling methanol. After cooling to room temp., the white solid precipitated was obtained by filtration, and residual solvent removed under vacuum overnight.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum, and residual thionyl chloride
  2. customremoved by co-evaporation with toluene
  3. customThe residue was recrystallized
  4. temperatureAfter cooling to room temp.
  5. customthe white solid precipitated
  6. customwas obtained by filtration, and residual solvent
  7. customremoved under vacuum overnight

Sources & evidence

ORD record
ord-48ae68d0e3d64aa49f0557037f2cbabe
Source dataset
uspto-grants-2001_01
Patent number
US06172076B2

Reaction notes

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