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

HRID 582439

反応式

HRID 582439 の反応式
[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]

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 962Water溶媒2 回HCID 1140Toluene溶媒2 回

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-a1ff9dcd14714eac927c69bd9159b305
出典データセット
uspto-grants-1999_07
特許番号
US05925152

関連ノート

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