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

HRID 1250480
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1250480
[F:1][C:2]([F:12])([F:11])[O:3][C:4]1[CH:5]=[C:6]([OH:10])[CH:7]=[CH:8][CH:9]=1.[H-].[Na+].Br[C:16]1[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18](Br)[N:17]=1.[CH3:25][N:26]([CH:28]=[O:29])C>CCCCCC>[C:25]1([NH:26][C:28]([C:16]2[CH:21]=[C:20]([O:22][CH3:23])[CH:19]=[C:18]([O:10][C:6]3[CH:7]=[CH:8][CH:9]=[C:4]([O:3][C:2]([F:11])([F:12])[F:1])[CH:5]=3)[N:17]=2)=[O:29])[CH:6]=[CH:5][CH:4]=[CH:9][CH:8]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 27332613-(Trifluoromethoxy)phenolHCID 109015692,6-Dibromo-4-methoxypyridine

Produkt 1

HCID 15906599N-phenyl-4-methoxy-6-{3-(trifluoromethoxy)phenoxy}-2-pyridine carboxamide

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8058
Hexane
Lösungsmittel

Reaktionsbedingungen

Temperatur
110 °C

Versuchsvorschrift

2.00 g (0.00937×1.2 mol) of 3-(trifluoromethoxy) phenol was dissolved in about 20 ml of DMF. The solution was further mixed with 0.39 g (ca. 60% in mineral oil; 0.00937×1.04 mol) of NaH and then with 2.50 g (0.00937 mol) of 2,6-dibromo-4-methoxy pyridine. After stirring at about 110° C. for about 4 hours, the obtained 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-f679f1a0be3743e791a0679138d9e2cb
Quelldatensatz
uspto-grants-2002_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US06339045B1

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