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

HRID 1420962Notes

Reaction equation

HRID 1420962 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-0a4055bee74942e5820a6fe7a61391ff
Source dataset
uspto-grants-2000_06
Patent number
US06071921

Reaction notes

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