Ethyl bromoacetate → HCID 21276952, compound

HRID 2292140Notes

Reaction equation

HRID 2292140 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:5]=2[N:6]=1.[H-].[Na+].Br[CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18]>O1CCCC1>[CH3:1][C:2]1[N:3]([CH2:16][C:17]([O:19][CH2:20][CH3:21])=[O:18])[C:4]2[CH:10]=[C:9]([CH3:11])[C:8]([CH3:12])=[CH:7][C:5]=2[N:6]=1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 768912,5,6-Trimethylbenzimidazole

Product 1

HCID 21276952HCID 21276952, compoundYield 93.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

2,5,6-Trimethylbenzimidazole (9.4 g) and sodium hydride (2.1 g, 80% suspension in oil) were sonicated in dry tetrahydrofuran (150 ml) for 1 hour. Ethyl 2-bromoacetate (9.8 g) in dry tetrahydrofuran (50 ml) was added and the reaction sonicated at 40° C. for 2 hours. The reaction was partitioned between ethyl acetate (300 ml) and water (100 ml), the organic phase dried over magnesium sulphate and the solvent removed under reduced pressure to yield ethyl 2-(2,5,6-trimethylbenzimidazol-1-yl)acetate (13.5 g).

Workup

  1. customthe reaction sonicated at 40° C. for 2 hours
  2. customThe reaction was partitioned between ethyl acetate (300 ml) and water (100 ml)
  3. dry with materialthe organic phase dried over magnesium sulphate
  4. customthe solvent removed under reduced pressure

Sources & evidence

ORD record
ord-9212763a91f4409b8c2a252854b5ae2b
Source dataset
uspto-grants-1989_01
Patent number
US04801598

Reaction notes

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