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Toluene → HCID 178439145, Verbindung

HRID 1297602
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1297602
[C:1]([C:3]([CH3:29])([CH3:28])[C:4]1[CH:27]=[CH:26][C:7]([CH2:8][NH:9][C:10](=[O:25])[C:11]2[CH:16]=[CH:15][CH:14]=[N:13][C:12]=2[O:17][C:18]2[CH:23]=[CH:22][C:21]([F:24])=[CH:20][CH:19]=2)=[CH:6][CH:5]=1)#[N:2].C1(C)C=CC=CC=1.C[Si]([N:41]=[N+:42]=[N-:43])(C)C.C[Sn](=O)C>CO>[F:24][C:21]1[CH:20]=[CH:19][C:18]([O:17][C:12]2[N:13]=[CH:14][CH:15]=[CH:16][C:11]=2[C:10]([NH:9][CH2:8][C:7]2[CH:26]=[CH:27][C:4]([C:3]([CH3:29])([C:1]3[NH:43][N:42]=[N:41][N:2]=3)[CH3:28])=[CH:5][CH:6]=2)=[O:25])=[CH:23][CH:22]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 75277DimethyloxostannaneHCID 78378AzidotrimethylsilaneHCID 69414857N-[4-(Cyano-dimethyl-methyl)-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide

Produkt 1

HCID 178439145HCID 178439145, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887
Methanol
Lösungsmittel

Reaktionsbedingungen

Temperatur
95 °C

Versuchsvorschrift

N-[4-(Cyano-dimethyl-methyl)-benzyl]-2-(4-fluoro-phenoxy)-nicotinamide (12.22 g) was placed in a sealable tube with anyhdrous toluene (10 mL). Trimethylsilyl azide (8.0 mL) and dimethyltin oxide (1.29 g) were then added. The reaction mixture was heated to 95° C. for 17 h, then allowed to cool to ambient temperature. Excess methanol was added and the mixture was concentrated to dryness in vacuo. Methanol was again added and evaporated. To the crude product were added ethyl acetate (200 mL) and and saturated aqueous sodium bicarbonate (100 mL) and water (100 mL). The aqueous layer was collected, and the organic layer extracted with 50% sodium bicarbonate twice (100 mL). The combined aqueous portions were separated and brought to pH 3 with conc. hydrochloric acid. The aqueous solution was then re-extracted with ethyl acetate (5×300 mL). The combined organics were dried over magnesium sulfate, filtered, and concentrated to dryness in vacuo. The crude product was purified by recrystallization (ethanol) to yield the title compound (5.36 g).

Aufarbeitung

  1. temperatureto cool to ambient temperature
  2. concentrationthe mixture was concentrated to dryness in vacuo
  3. additionMethanol was again added
  4. customevaporated
  5. additionTo the crude product were added ethyl acetate (200 mL) and and saturated aqueous sodium bicarbonate (100 mL) and water (100 mL)
  6. customThe aqueous layer was collected
  7. extractionthe organic layer extracted with 50% sodium bicarbonate twice (100 mL)
  8. customThe combined aqueous portions were separated
  9. extractionThe aqueous solution was then re-extracted with ethyl acetate (5×300 mL)
  10. dry with materialThe combined organics were dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated to dryness in vacuo
  13. customThe crude product was purified by recrystallization (ethanol)

Quellen und Nachweise

ORD-Eintrag
ord-a7d65b017bfd4a6ea15c000572610019
Quelldatensatz
uspto-grants-2007_07
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07250518B2

Notizen zur Reaktion

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