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Dimethylformamide → N-phenyl-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

HRID 1250478
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250478
[F:1][C:2]([F:11])([F:10])[C:3]1[CH:4]=[C:5]([OH:9])[CH:6]=[CH:7][CH:8]=1.[H-].[Na+].Br[C:15]1[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17](Br)[N:16]=1.[CH3:24][N:25](C)[CH:26]=[O:27]>CCCCCC>[C:24]1([NH:25][C:26]([C:15]2[CH:20]=[C:19]([O:21][CH3:22])[CH:18]=[C:17]([O:9][C:5]3[CH:6]=[CH:7][CH:8]=[C:3]([C:2]([F:10])([F:11])[F:1])[CH:4]=3)[N:16]=2)=[O:27])[CH:5]=[CH:4][CH:3]=[CH:8][CH:7]=1
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Komponenten

6

Edukt 4

HCID 6228Dimethylformamide2×HCID 73763-(Trifluoromethyl)phenolHCID 24758Sodium hydrideHCID 109015692,6-Dibromo-4-methoxypyridine

Produkt 1

HCID 15906594N-phenyl-4-methoxy-6-{3-(trifluoromethyl)phenoxy}-2-pyridine carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Reaktionsbedingungen

Temperatur
120 °C

Versuchsvorschrift

3.34 g (0.187×1.1 mol) of 3-(trifluoromethyl) phenol was dissolved in about 30 ml of dimethyl formamide (hereinafter referred to merely as “DMF”). The solution was further mixed with 0.78 g (ca. 60% in mineral oil; 0.0187×1.04 mol) of NaH and then with 5.00 g (0.0187 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 120° C. for about 2 hours, the resultant mixture was allowed to stand for cooling to room temperature. After the reaction solution was distributed in hexane-saturated sodium bicarbonate water, the organic phase of the obtained solution was washed with saturated brine and dried with anhydrous sodium sulfate. The resultant solution was concentrated and then purified by silica gel column chromatography (eluting solution: ethyl acetate/hexane), and the obtained eluate was subjected to recrystallization using hexane, thereby obtaining an aimed product.

Aufarbeitung

  1. temperaturefor cooling to room temperature
  2. washthe organic phase of the obtained solution was washed with saturated brine
  3. dry with materialdried with anhydrous sodium sulfate
  4. concentrationThe resultant solution was concentrated
  5. custompurified by silica gel column chromatography (eluting solution: ethyl acetate/hexane)
  6. customthe obtained eluate was subjected to recrystallization

Quellen und Nachweise

ORD-Eintrag
ord-e98d5922e892490e9986a215a316f0aa
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06339045B1

Notizen zur Reaktion

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