2-Methylbenzimidazole → 61981-79-1

HRID 2302319Notes

Reaction equation

HRID 2302319 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[CH:9][CH:8]=[CH:7][C:5]=2[N:6]=1.Cl.Cl[CH2:13][CH2:14][NH2:15].[OH-].[Na+]>S([O-])([O-])(=O)=O.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C(#N)C>[CH3:1][C:2]1[N:6]([CH2:13][CH2:14][NH2:15])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

6

Reactant 3

HCID 119842-MethylbenzimidazoleHCID 14798Sodium HydroxideHCID 97937372-Chloroethylamine hydrochloride

Product 1

HCID 437947761981-79-1Yield 54.5%

Reagents, catalysts & solvents 2

HCID 11433187Bis(tetrabutylammonium) sulphateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-methylbenzimidazole (4.93 g, 37.3 mmol), 2-chloroethylamine hydrochloride (4.67 g, 40.3 mmol), tetrabutylammonium sulfate (0.51 g, 1.5 mmol), sodium hydroxide (5.37 g, 134.2 mmol) and acetonitrile (80 mL) are stirred at reflux for 48 hrs. The resulting mixture is cooled to room temperature, filtered and concentrated in vacuo. The residue is purified by flash column chromatography (silica gel) using 1-3% MeOH—CH2Cl2 saturated with ammonium hydroxide as eluent to afford the title compound (3.56 g, MH+=176).

Workup

  1. temperatureat reflux for 48 hrs
  2. filtrationfiltered
  3. concentrationconcentrated in vacuo
  4. customThe residue is purified by flash column chromatography (silica gel)

Sources & evidence

ORD record
ord-a86b18220d5444e7a9fe501df7d9e29a
Source dataset
uspto-grants-2002_08
Patent number
US06432959B1

Reaction notes

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