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

HRID 1384581Notes

Reaction equation

HRID 1384581 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%). 1H NMR Spectrum: (DMSOd6; CF3COOD) 4.07(s, 3H); 5.38(s, 2H); 7.6-7.7(m, 2H); 7.9(d, 1H); 8.05(dd, 1H) MS-ESI: 181 [MH]+

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-c157ee06403740e6835235c08e2fd3b2
Source dataset
uspto-grants-2001_07
Patent number
US06258951B1

Reaction notes

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