Water → 2-(Cyanomethyl)thiophene-3-carbonitrile

HRID 1006944Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1006944
Br[CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9].[C-:10]#[N:11].[Na+].O>C1(C)C=CC=CC=1.C(OCC)(=O)C>[C:10]([CH2:2][C:3]1[S:4][CH:5]=[CH:6][C:7]=1[C:8]#[N:9])#[N:11]

Komponenten

6

Edukt 3

HCID 962WaterHCID 8929Sodium CyanideHCID 225036202-(Bromomethyl)thiophene-3-carbonitrile

Produkt 1

HCID 225034392-(Cyanomethyl)thiophene-3-carbonitrileAusbeute 43 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 1140TolueneLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-Bromomethyl-3-cyanothiophene (2.746 g) was dissolved in toluene (40 ml), followed by the addition of a solution of sodium cyanide (2.002 g)/water (15 ml), and the mixture was stirred at 80° C. overnight. The reaction mixture was diluted with ethyl acetate and washed with an aqueous solution of saturated sodium bicarbonate, dried (over MgSO4) and evaporated. The resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system), to give the title compound as a pale yellow solid (823 mg, yield; 43%).

Aufarbeitung

  1. washwashed with an aqueous solution of saturated sodium bicarbonate
  2. dry with materialdried (over MgSO4)
  3. customevaporated
  4. customThe resulting residue was purified by silica gel column chromatography (ethyl acetate/hexane system)

Quellen und Nachweise

ORD-Eintrag
ord-7c43bdfb337547ee812e8e288ae0532f
Quelldatensatz
uspto-grants-2004_09
Patentnummer
US06790844B2

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