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

HRID 443258Notes

Reaction equation

HRID 443258 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; Example 1, Step D) 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 was 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 was removed under vacuum overnight.

Workup

  1. concentrationThe resultant mixture was concentrated under vacuum, and residual thionyl chloride
  2. customwas removed 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. customwas removed under vacuum overnight

Sources & evidence

ORD record
ord-6f51f6bdd3e245b0b51e5ad598be43f8
Source dataset
uspto-grants-1999_04
Patent number
US05891889

Reaction notes

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