Sodium Iodide → 2,3-Dicyanonaphthalene

HRID 2082273

Reaktionsgleichung

Reaktionsgleichung von HRID 2082273
[I-].[Na+].Br[CH:4](Br)[C:5]1[C:6]([CH:11](Br)Br)=[CH:7][CH:8]=[CH:9][CH:10]=1.[C:15](#[N:20])/[CH:16]=[CH:17]/[C:18]#[N:19].S([O-])(O)=O.[Na+]>CN(C)C=O>[C:18]([C:17]1[C:16]([C:15]#[N:20])=[CH:11][C:6]2[C:5](=[CH:10][CH:9]=[CH:8][CH:7]=2)[CH:4]=1)#[N:19]

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 832341,2-Bis(dibromomethyl)benzeneHCID 637930FumaronitrileHCID 23665763Sodium Bisulfite2×

Produkt 1

HCID 6012702,3-DicyanonaphthaleneAusbeute 73 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
75 °C

Versuchsvorschrift

One hundred grams (0.67 mole) of sodium iodide was added to a well-stirred solution of 42.2 g (0.1 mole) of α,α,α',α'-tetrabromo-o-xylene and 13.5 g (0.173 mole) of fumaronitrile in 400 ml of anhydrous N,N-dimethylformamide, and the resulting mixture was stirred at 75° C. for about 7 hours in an atmosphere of nitrogen. After the reaction, the mixture was poured into about 2 kg of ice, and thereto was slowly added sodium hydrogen sulfite until the red-brown colored aqueous solution turned to light yellow. After adding a slightly excessive quantity of sodium hydrogen sulfite, the resulting mixture was stirred for a while and then allowed to stand overnight at room temperature. The deposited light yellow-colored solid product was collected by filtration with suction, thoroughly washed with water, and allowed to dry. The light yellow-colored solid product thus obtained was recrystallized from ethanol/chloroform mixture to obtain 13 g (73%) of 2,3-dicyanonaphthalene as a colorless crystalline material.

Aufarbeitung

  1. customAfter the reaction
  2. stirringthe resulting mixture was stirred for a while
  3. waitto stand overnight at room temperature
  4. filtrationThe deposited light yellow-colored solid product was collected by filtration with suction
  5. washthoroughly washed with water
  6. customto dry
  7. customThe light yellow-colored solid product thus obtained
  8. customwas recrystallized from ethanol/chloroform mixture

Quellen und Nachweise

ORD-Eintrag
ord-1e55558865f74cd4952cee46b45e521f
Quelldatensatz
uspto-grants-1993_02
Patentnummer
US05188922

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