Ethyl bromoacetate → 1-(ethoxycarbonylmethyl)-2-chlorobenzimidazole

HRID 573316Notes

Reaction equation

HRID 573316 reaction equation
[Cl:1][C:2]1[NH:6][C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1.[H-].[Na+].Br[CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16]>CN(C=O)C>[Cl:1][C:2]1[N:6]([CH2:14][C:15]([O:17][CH2:18][CH3:19])=[O:16])[C:5]2[CH:7]=[CH:8][CH:9]=[CH:10][C:4]=2[N:3]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 785722-Chlorobenzimidazole

Product 1

HCID 41591541-(ethoxycarbonylmethyl)-2-chlorobenzimidazole

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 2-chloro-1H-benzo[d]imidazole (10 g) and NaH (60% in oil, 3.15 g) in DMF (150 mL) was added ethyl bromoacetate (11.0 mL) at 0° C. After stirring overnight at room temperature, the reaction mixture was quenched with water and extracted with AcOEt. The extract was washed with water and brine, dried over MgSO4, and concentrated under reduced pressure. The precipitate was crystallized from AcOEt/hexane to give the title compound (12 g).

Workup

  1. customthe reaction mixture was quenched with water
  2. extractionextracted with AcOEt
  3. washThe extract was washed with water and brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated under reduced pressure
  6. customThe precipitate was crystallized from AcOEt/hexane

Sources & evidence

ORD record
ord-cd7f19ad502742fb9a4c7b9f7c6961cb
Source dataset
uspto-grants-2015_05
Patent number
US09029536B2

Reaction notes

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