Acetic Acid → (E)-3-(2,5-difluoro-phenylamino)-but-2-enoic acid ethyl ester

HRID 47422

反応式

HRID 47422 の反応式
[F:1][C:2]1[CH:8]=[CH:7][C:6]([F:9])=[CH:5][C:3]=1[NH2:4].[C:10]([O:16][CH2:17][CH3:18])(=[O:15])[CH2:11][C:12]([CH3:14])=O.C(O)(=O)C>C1(C)C=CC=CC=1>[CH2:17]([O:16][C:10](=[O:15])/[CH:11]=[C:12](/[NH:4][C:3]1[CH:5]=[C:6]([F:9])[CH:7]=[CH:8][C:2]=1[F:1])\[CH3:14])[CH3:18]

参加物

5

反応物 3

HCID 176Acetic AcidHCID 8868Ethyl AcetoacetateHCID 677752,5-Difluoroaniline

生成物 1

HCID 69831932(E)-3-(2,5-difluoro-phenylamino)-but-2-enoic acid ethyl ester

試薬・触媒・溶媒 1

HCID 1140Toluene溶媒

実験手順

A mixture of 2,5-difluoroaniline (7.5 ml) and ethyl acetoacetate (9.6 ml) were combined in toluene (15 ml) containing acetic acid (1.5 ml). The mixture was boiled under Dean-Stark azeotrope conditions, cooled and solvent removed at reduced pressure to give crude (E)-3-(2,5-difluoro-phenylamino)-but-2-enoic acid ethyl ester (16.17 g). (E)-3-(2,5-Difluoro-phenylamino)-but-2-enoic acid ethyl ester (2 g) was refluxed in Dowtherm-A (40 ml) for 3 h. After cooling the Dowtherm was diluted with pentane (40 ml) and the precipitated title compound isolated by filtration. (Method A). 1H NMR δ: 2.34 (3H, s), 5.91 (1H, s), 6.96 (1H, m), 7.53 (1H, m), 11.48 (1H, brs).

後処理

  1. temperaturecooled
  2. customsolvent removed at reduced pressure

出典と根拠

ORDレコード
ord-c39fd919c8284adaa87ad8d8906fc7d0
出典データセット
uspto-grants-2004_03
特許番号
US06699879B1

関連ノート

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