Benzimidazole → 1-(2-methoxyethyl)benzimidazole

HRID 851841Notes

Reaction equation

HRID 851841 reaction equation
[N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[NH:3][CH:2]=1.[CH3:10][O:11][CH2:12][CH2:13]Cl.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O>[CH3:10][O:11][CH2:12][CH2:13][N:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 5798BenzimidazoleHCID 11430Potassium CarbonateHCID 123162-Chloroethyl methyl ether

Product 1

HCID 19732251-(2-methoxyethyl)benzimidazoleYield 87.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

In a nitrogen atmosphere, a mixture of 118 g of benzimidazole, 94.5 g of 2-chloroethyl methyl ether, 138 g of potassium carbonate, and 400 g of N,N-dimethylformamide was heated and stirred at 100° C. for 20 hours. The reaction mixture was subjected to conventional aqueous work-up and distillation under reduced pressure for purification, to give 154 g of 1-(2-methoxyethyl)-1H-benzimidazole (boiling point 125° C./33 Pa, yield 87%).

Workup

  1. temperaturewas heated
  2. distillationThe reaction mixture was subjected to conventional aqueous work-up and distillation under reduced pressure for purification

Sources & evidence

ORD record
ord-f30f642e4ce54ff2b1f405bfba891e9e
Source dataset
uspto-grants-2007_08
Patent number
US07252925B2

Reaction notes

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