Furfurylamine → 2-Amino-1-(2-furanylmethyl)-4,5-difuryl-3-pyrrolecarbonitrile

HRID 582439

Reaktionsgleichung

Reaktionsgleichung von HRID 582439
[CH:1]1[CH:5]=[C:4]([CH:6](O)[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)=O)[O:3][CH:2]=1.[CH2:15]([NH2:21])[C:16]1[O:20][CH:19]=[CH:18][CH:17]=1.C1(C)C=CC(S(O)(=O)=O)=CC=1.[C:33](#[N:37])[CH2:34][C:35]#[N:36]>C1(C)C=CC=CC=1.O>[NH2:37][C:33]1[N:21]([CH2:15][C:16]2[O:20][CH:19]=[CH:18][CH:17]=2)[C:7]([C:9]2[O:13][CH:12]=[CH:11][CH:10]=2)=[C:6]([C:4]2[O:3][CH:2]=[CH:1][CH:5]=2)[C:34]=1[C:35]#[N:36]

Komponenten

7

Edukt 4

HCID 3438FurfurylamineHCID 6101p-Toluenesulfonic acidHCID 8010MalononitrileHCID 11100Furoin

Produkt 1

HCID 232176052-Amino-1-(2-furanylmethyl)-4,5-difuryl-3-pyrrolecarbonitrile

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 962WaterLösungsmittel2×HCID 1140TolueneLösungsmittel2×

Versuchsvorschrift

2-amino-1-(2-furanylmethyl)-4,5-difuryl-3-pyrrolecarbonitrile was prepared as follows: 300 g (1.56 mol) of Furoin (ex Aldrich) was reacted with 151.6 g (1.56 mol) of furfurylamine in the presence of 1.5 g of p-toluenesulphonic acid in toluene under stirring and reflux. The water produced was removed via a Dean Stark trap. When formation of water had ceased (31 ml removed), 103.1 g (1.56 mol) of malononitrile was added as a dispersion in 100 ml toluene, reflux was continued. When again formation of water had ceased (26 ml removed via the Dean Stark trap), the reaction mixture was cooled and the toluene was removed by evaporation. In this way 498 g of a black solid product was obtained. Subsequently, 100 g of this product was purified by flash chromatography (silica, hexane/ethyl acetate as eluant) and 24 g of the product was recovered.

Aufarbeitung

  1. temperaturereflux
  2. customwas removed via a Dean Stark trap
  3. temperaturereflux
  4. customremoved via the Dean Stark trap), the reaction mixture
  5. temperaturewas cooled
  6. customthe toluene was removed by evaporation

Quellen und Nachweise

ORD-Eintrag
ord-a1ff9dcd14714eac927c69bd9159b305
Quelldatensatz
uspto-grants-1999_07
Patentnummer
US05925152

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