Sodium Chloride → Propanoic acid, 2-(4-((6,7-dichloro-2-quinoxalinyl)oxy)phenoxy)-, methyl ester

HRID 64575

Reaktionsgleichung

Reaktionsgleichung von HRID 64575
[OH:1][C:2]1[CH:14]=[CH:13][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:4][CH:3]=1.[H-].[Na+].[H][H].Cl[C:20]1[CH:29]=[N:28][C:27]2[C:22](=[CH:23][C:24]([Cl:31])=[C:25]([Cl:30])[CH:26]=2)[N:21]=1.[Cl-].[Na+]>CN(C)C=O>[Cl:30][C:25]1[CH:26]=[C:27]2[C:22](=[CH:23][C:24]=1[Cl:31])[N:21]=[C:20]([O:1][C:2]1[CH:3]=[CH:4][C:5]([O:6][CH:7]([CH3:12])[C:8]([O:10][CH3:11])=[O:9])=[CH:13][CH:14]=1)[CH:29]=[N:28]2

Komponenten

7

Edukt 5

HCID 5234Sodium ChlorideHCID 24758Sodium hydrideHCID 366926Propanoic acid, 2-(4-hydroxyphenoxy)-, methyl esterHCID 100369782,6,7-TrichloroquinoxalineHCID 178418361HCID 178418361, Verbindung

Produkt 1

HCID 187100Propanoic acid, 2-(4-((6,7-dichloro-2-quinoxalinyl)oxy)phenoxy)-, methyl ester

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

In a nitrogen atmosphere, a solution of 3.9 g (0.02 mole) methyl 2-(4-hydroxyphenoxy)propanoate in 20 cc of dimethylformamide was added dropwise at about 15° C. to a suspension of 0.8 g sodium hydride in 10 cc dimethylformamide. When the evolution of hydrogen ceased, 4.7 g of (0.02 mole) 2,6,7-trichloroquinoxaline was added and the reaction mixture was heated for 5 hours at ~130° C. Filtering the reaction mixture yielded a small amount of insoluble material. The filtrate was poured into approximately 200 cc of ice-water. Sodium chloride was added to the solution which was then extracted with 1200 cc of ether (4×300). The ethereal extracts were combined and dried over magnesium sulfate. The ether was removed under vacuum and the crude product was crystallized from CH3OH. Yield 2.8 g, m.p. 100°-105°.

Aufarbeitung

  1. temperaturethe reaction mixture was heated for 5 hours at ~130° C
  2. filtrationFiltering the reaction mixture
  3. customyielded a small amount of insoluble material
  4. extractionwas then extracted with 1200 cc of ether (4×300)
  5. dry with materialdried over magnesium sulfate
  6. customThe ether was removed under vacuum
  7. customthe crude product was crystallized from CH3OH

Quellen und Nachweise

ORD-Eintrag
ord-838dd883dd6b4c7281091294dd3bc776
Quelldatensatz
uspto-grants-1986_09
Patentnummer
US04609396

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