Ethyl bromoacetate → 6-chloro-2-ethyl-1-ethoxycarbonylmethyl-1H-imidazo[4,5-b]quinoxaline

HRID 2397548

Reaktionsgleichung

Reaktionsgleichung von HRID 2397548
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[NH:12][C:13]([CH2:15][CH3:16])=[N:14][C:6]1=[N:5]2.C(=O)([O-])[O-].[K+].[K+].Br[CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26]>CN(C)C=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]=[C:7]1[N:12]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[C:13]([CH2:15][CH3:16])=[N:14][C:6]1=[N:5]2

Komponenten

5

Edukt 3

HCID 7748Ethyl bromoacetateHCID 11430Potassium CarbonateHCID 1784375416-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline

Produkt 1

HCID 214359666-chloro-2-ethyl-1-ethoxycarbonylmethyl-1H-imidazo[4,5-b]quinoxaline

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

A mixture of 100 parts of 6-chloro-2-ethyl-1H-imidazo[4,5-b]quinoxaline, 70 parts of anhydrous potassium carbonate, 75 parts of ethyl bromoacetate, and 600 parts of anhydrous dimethylformamide was heated at 100° for 2.5 hours. The mixture was filtered and the crude product was precipitated from the filtrate by addition of 1200 parts of water, collected by filtration, washed with water, ethanol, and ether, and airdried. Recrystallization from 95% ethanol afforded 63 parts of 6-chloro-2-ethyl-1-ethoxycarbonylmethyl-1H-imidazo[4,5-b]quinoxaline, m.p. 174°-175°.

Aufarbeitung

  1. temperaturewas heated at 100° for 2.5 hours
  2. filtrationThe mixture was filtered
  3. customthe crude product was precipitated from the filtrate by addition of 1200 parts of water
  4. filtrationcollected by filtration
  5. washwashed with water, ethanol, and ether
  6. customRecrystallization from 95% ethanol

Quellen und Nachweise

ORD-Eintrag
ord-2d02fb0618364871867ce677d5505903
Quelldatensatz
uspto-grants-1977_05
Patentnummer
US04022777

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