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

HRID 1737530Notes

Reaction equation

HRID 1737530 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-471ae0d399634d31ae98453389163925
Source dataset
uspto-grants-1999_10
Patent number
US05962458

Reaction notes

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