Ethyl bromoacetate → Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetate

HRID 2187050Notes

Reaction equation

HRID 2187050 reaction equation
[H-].[Na+].[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[NH:12][C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)[CH3:4].Br[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>O1CCCC1>[CH2:3]([C:5]1[CH:6]=[CH:7][C:8]([C:11]2[N:12]([CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[C:13](=[O:20])[C:14]([CH:17]([CH3:19])[CH3:18])([CH3:16])[N:15]=2)=[N:9][CH:10]=1)[CH3:4]

Participants

5

Reactant 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 133398183-Descarboxy Imazethapyr

Product 1

HCID 22450190Ethyl 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline-1-acetate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

A stirred mixture of sodium hydride (0.45 g, 15 mmol, 80% oil dispersion) in anhydrous tetrahydrofuran is treated with a solution of 2-(5-ethyl-2-pyridyl)-4-isopropyl-4-methyl-5-oxo-2-imidazoline (3.30 g, 13.47 mmol) in anhydrous tetrahydrofuran dropwise over the course of 40 minutes. After addition is complete and the initial effervescence subsides, ethyl bromoacetate (2.30 g, 13.50 mmol) is added to the reaction mixture. After 24 hours stirring at room temperature under nitrogen, the reaction mixture is partitioned between water and ether. The layers are separated, and the organic layer is dried over magnesium sulfate, vacuum filtered through diatomaceous earth and concentrated in vacuo to obtain a residue. The residue is purified by flash chromatography (2:1 hexanes/ethyl acetate eluent) to give the title product as a pale yellow oil.

Workup

  1. additionAfter addition
  2. customthe reaction mixture is partitioned between water and ether
  3. customThe layers are separated
  4. dry with materialthe organic layer is dried over magnesium sulfate, vacuum
  5. filtrationfiltered through diatomaceous earth
  6. concentrationconcentrated in vacuo
  7. customto obtain a residue
  8. customThe residue is purified by flash chromatography (2:1 hexanes/ethyl acetate eluent)

Sources & evidence

ORD record
ord-ee25145da3e8476f9ac4ee32543e4bac
Source dataset
uspto-grants-2002_06
Patent number
US06407217B1

Reaction notes

Loading…