Thionyl Chloride → 2-(Chloromethyl)-1-methylbenzimidazole

HRID 279567

Reaction equation

HRID 279567 reaction equation
O[CH2:2][C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1.S(Cl)([Cl:15])=O>>[Cl:15][CH2:2][C:3]1[N:7]([CH3:8])[C:6]2[CH:9]=[CH:10][CH:11]=[CH:12][C:5]=2[N:4]=1

Participants

3

Reactant 2

HCID 24386Thionyl ChlorideHCID 344177(1-methyl-1H-1,3-benzodiazol-2-yl)methanol

Product 1

HCID 2480442-(Chloromethyl)-1-methylbenzimidazoleYield 36%

Procedure

A solution of 2-hydroxymethyl-1-methylbenzimidazole (1.1 g, 6.7 mmol) in thionyl chloride (10 ml) was stirred at ambient temperature for 15 minutes and then heated at reflux for 15 minutes. The volatiles were removed by evaporation and the residue purified by column chromatography eluting with methylene chloride/methanol (95/5) to give 2-chloromethyl-1-methylbenzimidazole (506 mg, 36%).

Workup

  1. temperatureheated
  2. temperatureat reflux for 15 minutes
  3. customThe volatiles were removed by evaporation
  4. customthe residue purified by column chromatography
  5. washeluting with methylene chloride/methanol (95/5)

Sources & evidence

ORD record
ord-d8c3115e42f34c5791ca6054fb4ab195
Source dataset
uspto-grants-2002_03
Patent number
US06362336B1

Linked notes

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