Hexamethylenetetramine → 5-Formylthiophene-2-Carbonitrile

HRID 35925

Reaktionsgleichung

Reaktionsgleichung von HRID 35925
Br[CH2:2][C:3]1[S:7][C:6]([C:8]#[N:9])=[CH:5][CH:4]=1.CC1SC(C#N)=CC=1.BrN1C(=[O:24])CCC1=O.C1N2CN3CN(C2)CN1C3>C(Cl)(Cl)(Cl)Cl.C(Cl)(Cl)Cl.C(O)(=O)C.C(OOC(=O)C1C=CC=CC=1)(=O)C1C=CC=CC=1.O>[C:8]([C:6]1[S:7][C:3]([CH:2]=[O:24])=[CH:4][CH:5]=1)#[N:9]

Komponenten

10

Edukt 4

HCID 4101HexamethylenetetramineHCID 67184N-bromobutanimideHCID 3127335-Methylthiophene-2-carbonitrileHCID 105600165-(Bromomethyl)thiophene-2-carbonitrile

Produkt 1

HCID 122800045-Formylthiophene-2-CarbonitrileAusbeute 44,8 %

Reagenzien, Katalysatoren, Lösungsmittel 5

HCID 7187Benzoyl PeroxideKatalysatorHCID 176Acetic AcidLösungsmittelHCID 962WaterLösungsmittelHCID 5943Carbon TetrachlorideLösungsmittelHCID 6212ChloroformLösungsmittel

Versuchsvorschrift

8 g of 5-bromomethylthiophene-2-carbonitrile (prepared by brominating 5.7 g of 5-methylthiophene-2-carbonitrile and 8.42 g of N-bromosuccinimide in 68 ml of carbon tetrachloride under exposure to light and with the addition of 185 mg of benzoyl peroxide) is refluxed for 30 minutes in 35 ml of chloroform with 5.6 g of hexamethylenetetramine. The precipitated salt is suctioned off and refluxed in 30 ml of acetic acid and 30 ml of water for 2 hours. After extraction with ether, washing of the ether phase with water, drying, and evaporation, 2.43 g of 5-cyanothiophene-2-aldehyde is obtained.

Aufarbeitung

  1. extractionAfter extraction with ether
  2. washwashing of the ether phase with water
  3. customdrying
  4. customevaporation

Quellen und Nachweise

ORD-Eintrag
ord-1f3ba0281163402181652b3d126f3b54
Quelldatensatz
uspto-grants-1995_05
Patentnummer
US05411982

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