Ethyl bromoacetate → HCID 21254672, compound

HRID 636483Notes

Reaction equation

HRID 636483 reaction equation
[CH2:1]([C:3]1[NH:7][C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=3)[C:5]=2[N:4]=1)[CH3:2].Br[CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25].C(=O)([O-])[O-].[K+].[K+].C(OCC)(=O)C>CN(C)C=O.O>[CH2:27]([O:26][C:24]([CH2:23][N:7]1[C:6]2[CH:8]=[CH:9][CH:10]=[C:11]([O:12][CH2:13][C:14]3[CH:15]=[CH:16][C:17]([O:20][CH3:21])=[CH:18][CH:19]=3)[C:5]=2[N:4]=[C:3]1[CH2:1][CH3:2])=[O:25])[CH3:28]

Participants

7

Reactant 4

HCID 7748Ethyl bromoacetateHCID 8857Ethyl AcetateHCID 11430Potassium CarbonateHCID 21254783HCID 21254783, compound

Product 1

HCID 21254672HCID 21254672, compoundYield 66.6%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

A solution of 2-ethyl-4-(4-methoxybenzyloxy)-1H-benzimidazole (282 mg), ethyl bromoacetate (184 mg) and potassium carbonate (414 mg) in dimethylformamide (3 ml) was stirred for 2 hours, and to the reaction mixture were added ethyl acetate and water. The separated organic layer was washed with brine, dried over magnesium sulfate and evaporated in vacuo. The residue was purified by flash chromatography (ethyl acetate:n-hexane =1:2 to 2:1, v/v) to give 1-ethoxycarbonylmethyl-2-ethyl-4-(4-methoxybenzyloxy)-1H-benzimidazole (245 mg) as white powder.

Workup

  1. washThe separated organic layer was washed with brine
  2. dry with materialdried over magnesium sulfate
  3. customevaporated in vacuo
  4. customThe residue was purified by flash chromatography (ethyl acetate

Sources & evidence

ORD record
ord-9e1e3fabc9e94c2abc86191d759ee871
Source dataset
uspto-grants-2001_02
Patent number
US06194396B1

Reaction notes

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