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

HRID 2080732Notes

Reaction equation

HRID 2080732 reaction equation
O[CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=1.S(Cl)([Cl:11])=O>>[ClH:11].[Cl:11][CH2:2][C:3]1[N:4]([CH3:8])[CH:5]=[CH:6][N:7]=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 hydrochloride

Conditions

Temperature
65 °C

Procedure

The compound (56.1 g) obtained in Example 10-1 was gradually added to thionyl chloride (119 ml) under ice-cooling. After completion of dropping, the whole was refluxed at 65° C. for 15 minutes. Excess thionyl chloride was distilled off under reduced pressure and the solution was further subjected to azeotropic distillation with toluene, thereby obtaining a hydrochloride (82.4 g) of the subject compound as a yellow solid.

Workup

  1. temperaturecooling
  2. distillationExcess thionyl chloride was distilled off under reduced pressure
  3. distillationthe solution was further subjected to azeotropic distillation with toluene

Sources & evidence

ORD record
ord-1db0528c9b4d418e82eff48a3d66eeec
Source dataset
uspto-grants-2011_04
Patent number
US07932281B2

Reaction notes

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