Ethyl bromoacetate → HCID 13059431, compound

HRID 223344Notes

Reaction equation

HRID 223344 reaction equation
[N:1]1([C:6]2[CH:11]=[CH:10][C:9]([C:12](=[O:18])[CH2:13][C:14](OC)=O)=[CH:8][CH:7]=2)[CH:5]=[CH:4][N:3]=[CH:2]1.[H-].[Na+].BrC[C:23]([O:25]CC)=[O:24]>O1CCCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([C:12](=[O:18])[CH2:13][CH2:14][C:23]([OH:25])=[O:24])=[CH:10][CH:11]=2)[CH:5]=[CH:4][N:3]=[CH:2]1

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 13059430HCID 13059430, compound

Product 1

HCID 13059431HCID 13059431, compoundYield 54%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A solution of methyl 4-(1H-imidazol-1-yl)-β-oxobenzenepropanoate (6.1 g, 0.025 mol) in tetrahydrofuran (65 ml) is added slowly to a stirred suspension of 50% NaH (1.2 g, 0.025 mol) in tetrahydrofuran (20 ml) and the solution is stirred for one additional hour. Ethyl bromoacetate (4.5 g) is added followed by refluxing the mixture for 7 to 8 hours. The tetrahydrofuran is removed, the residue is treated with water, and the organic material is extracted with ether. The residue obtained after removal of ether is hydrolysed by heating with 6 N HCl for 7 to 8 hours. The crude acid is finally crystallized from dimethylformamide to yield 3.3 g of the product 4-(1H-imidazol-1-yl)-γ-oxobenzenebutanoic acid.

Workup

  1. temperatureby refluxing the mixture for 7 to 8 hours
  2. customThe tetrahydrofuran is removed
  3. additionthe residue is treated with water
  4. extractionthe organic material is extracted with ether
  5. customThe residue obtained
  6. customafter removal of ether
  7. temperatureby heating with 6 N HCl for 7 to 8 hours
  8. customThe crude acid is finally crystallized from dimethylformamide

Sources & evidence

ORD record
ord-8c1af3a66af94737afaa498744771152
Source dataset
uspto-grants-1982_10
Patent number
US04353905

Reaction notes

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