Thionyl Chloride → 716318-71-7

HRID 1786099Notes

Reaction equation

HRID 1786099 reaction equation
[C:1]1([N:7]2[CH:11]=[CH:10][N:9]=[C:8]2[CH2:12]O)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.O=S(Cl)[Cl:16]>>[ClH:16].[Cl:16][CH2:12][C:8]1[N:7]([C:1]2[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=2)[CH:11]=[CH:10][N:9]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 277166(1-Phenyl-1H-imidazol-2-yl)methanol

Product 1

HCID 24278882716318-71-7Yield 74%

Conditions

Temperature
0 °C

Procedure

27 g (0.179 mol) of (1-phenyl-1H-imidazol-2-yl)methanol were added to 25 ml of SOCl2 under stirring at 0° C. The solution obtained was refluxed for 30 min and then the excess SOCl2 removed under vacuum. The thus obtained residue was recrystallized from 50 ml of a mixture of toluene:EtOH=5:1 to give 16.6 g (74%) of 2-(chloromethyl)-1-phenyl-1H-imidazole hydrochloride.

Workup

  1. customThe solution obtained
  2. temperaturewas refluxed for 30 min
  3. customthe excess SOCl2 removed under vacuum
  4. customThe thus obtained residue was recrystallized from 50 ml of a mixture of toluene

Sources & evidence

ORD record
ord-c203e45701fe42a9b1d05b7dac5069b2
Source dataset
uspto-grants-2009_03
Patent number
US07507688B2

Reaction notes

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