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

HRID 1068439Notes

Reaction equation

HRID 1068439 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-2b321119f5fa4c13a0036e01ebc000a0
Source dataset
uspto-grants-2001_06
Patent number
US06248756B1

Reaction notes

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