Thionyl Chloride → 2-(Chloromethyl)-1-methylbenzimidazole
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]=1Participants
3
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
- temperatureheated
- temperatureat reflux for 15 minutes
- customThe volatiles were removed by evaporation
- customthe residue purified by column chromatography
- washeluting with methylene chloride/methanol (95/5)
Sources & evidence
- ORD record
- ord-d8c3115e42f34c5791ca6054fb4ab195
- Source dataset
- uspto-grants-2002_03
- Patent number
- US06362336B1
Reaction notes
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