Water → 2-Nitro-5-(4-chlorophenoxy)benzonitrile

HRID 52659

Reaktionsgleichung

Reaktionsgleichung von HRID 52659
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([OH:8])=[CH:4][CH:3]=1.Cl[C:10]1[CH:11]=[CH:12][C:13]([N+:18]([O-:20])=[O:19])=[C:14]([CH:17]=1)[C:15]#[N:16].O.[OH-].[Na+]>CN(C)C=O>[N+:18]([C:13]1[CH:12]=[CH:11][C:10]([O:8][C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[CH:17][C:14]=1[C:15]#[N:16])([O-:20])=[O:19]

Komponenten

6

Edukt 4

HCID 962WaterHCID 46844-ChlorophenolHCID 14798Sodium HydroxideHCID 1005065-Chloro-2-nitrobenzonitrile

Produkt 1

HCID 218248742-Nitro-5-(4-chlorophenoxy)benzonitrileAusbeute 52,6 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Sodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether. The petroleum ether was decanted, and the sodium hydride was suspended in about 20 mL of N,N-dimethylformamide. The suspension was stirred, and solutions of 4.5 grams (0.035 mole) of 4-chlorophenol in 20 mL of N,N-dimethylformamide and 5.0 grams (0.027 mole) of 5-chloro-2-nitrobenzonitrile in 20 mL of N,N-dimethylformamide were added, respectively. Upon completion of addition, the reaction mixture was warmed to reflux where it stirred for about 18 hours. The reaction mixture was then cooled and poured into a mixture of 500 mL of water and 50 mL of aqueous 2N sodium hydroxide. The mixture was stirred for about 15 minutes, then it was allowed to stand for about 18 hours. The resultant solid was collected by filtration and recrystallized from ethanol, yielding 3.9 grams of 2-nitro-5-(4-chlorophenoxy)benzonitrile, mp 120°-122° C. The NMR spectrum was consistent with the proposed structure.

Aufarbeitung

  1. washSodium hydride (60% in mineral oil), 1.5 grams (0.038 mole) was washed in petroleum ether
  2. customThe petroleum ether was decanted
  3. additionUpon completion of addition
  4. temperaturethe reaction mixture was warmed
  5. temperatureto reflux where it
  6. stirringstirred for about 18 hours
  7. temperatureThe reaction mixture was then cooled
  8. stirringThe mixture was stirred for about 15 minutes
  9. filtrationThe resultant solid was collected by filtration
  10. customrecrystallized from ethanol

Quellen und Nachweise

ORD-Eintrag
ord-a9a2d6ca0ed744a9a393d850761854eb
Quelldatensatz
uspto-grants-1997_04
Patentnummer
US05616718

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