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

HRID 2187050노트

반응식

HRID 2187050 반응식
[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]

참가 물질

5

반응물 3

HCID 7748Ethyl bromoacetateHCID 24758Sodium hydrideHCID 133398183-Descarboxy Imazethapyr

생성물 1

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

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-ee25145da3e8476f9ac4ee32543e4bac
출처 데이터셋
uspto-grants-2002_06
특허 번호
US06407217B1

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