Thionyl Chloride → 1-benzyl-2-(chloromethyl)-1H-imidazole

HRID 1253030Notes

Reaction equation

HRID 1253030 reaction equation
[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13]O)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)([Cl:17])=O>>[CH2:1]([N:8]1[CH:12]=[CH:11][N:10]=[C:9]1[CH2:13][Cl:17])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 311778(1-benzyl-1H-imidazol-2-yl)methanol

Product 1

HCID 7367921-benzyl-2-(chloromethyl)-1H-imidazoleYield 93.5%

Procedure

A mixture of 10 gm (45 mmole) of N-benzyl-2-hydroxymethylimidazole and 11 gm (92 mmole) of thionyl chloride was stirred at room temperature for 30 minutes before it was heated to reflux for 30 minutes. The excess thionyl chloride was removed under reduced pressure. The resultant residue (10 gm crude) was crystallized from ethanol/ether to obtain 8.7 gm of N-benzyl-2-chloromethylimidazole, m.p. 180°-182° C.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 30 minutes
  3. customThe excess thionyl chloride was removed under reduced pressure
  4. customThe resultant residue (10 gm crude) was crystallized from ethanol/ether

Sources & evidence

ORD record
ord-39fad1f746cd4c8a807fe30658bab454
Source dataset
uspto-grants-1988_05
Patent number
US04746669

Reaction notes

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