Thionyl Chloride → 2-(chloromethyl)-1-methyl-1H-imidazole hydrochloride

HRID 1786097Notes

Reaction equation

HRID 1786097 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][N:4]=[C:3]1[CH2:7]O.O=S(Cl)[Cl:11]>>[ClH:11].[Cl:11][CH2:7][C:3]1[N:2]([CH3:1])[CH:6]=[CH:5][N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 573612(1-methyl-1H-imidazol-2-yl)methanol

Product 1

HCID 27954062-(chloromethyl)-1-methyl-1H-imidazole hydrochlorideYield 69%

Conditions

Temperature
0 °C

Procedure

20 g (0.179 mol) of (1-methyl-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 45 ml of EtOH to give 20.5 g (69%) of 2-(chloromethyl)-1-methyl-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 45 ml of EtOH

Sources & evidence

ORD record
ord-d675fd71c5f64e3aa5cff22a2210eb43
Source dataset
uspto-grants-2009_03
Patent number
US07507688B2

Reaction notes

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