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

HRID 582439

반응식

HRID 582439 반응식
[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]

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 962Water용매2회HCID 1140Toluene용매2회

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-a1ff9dcd14714eac927c69bd9159b305
출처 데이터셋
uspto-grants-1999_07
특허 번호
US05925152

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