2-Methoxyaniline → o-[2-Ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole

HRID 2379426ノート

反応式

HRID 2379426 の反応式
[CH3:1][O:2][C:3]1[C:4]([NH2:9])=[CH:5][CH:6]=[CH:7][CH:8]=1.[CH2:10]([O:12][C:13](=[O:24])[CH2:14][C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH3:11].[CH:25](OCC)(OCC)OCC>C(O)C>[CH2:10]([O:12][C:13]([CH:14]([C:15](=[O:23])[CH2:16][CH2:17][C:18]([O:20][CH2:21][CH3:22])=[O:19])[CH:25]=[N:9][C:4]1[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=1[O:2][CH3:1])=[O:24])[CH3:11]

参加物

5

反応物 3

HCID 70002-MethoxyanilineHCID 31214Ethyl orthoformateHCID 81576Diethyl 3-oxoadipate

生成物 1

HCID 18957128o-[2-Ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole収率 82%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
20 °C

実験手順

A mixture consisting of 5.0 g (0.041 mole) of o-anisidine (available from the Aldrich Chemical Company, Inc. of Milwaukee, Wis.), 8.86 g (0.041 mole) of β-ketoadipic acid diethyl ester (available from Sigma Chemical Company of St. Louis, Mo.) and 6.07 g (0.041 mole) of triethyl orthoformate (also available from Aldrich) was placed in an open reaction flask and heated to 140° C. for a period of three hours, at which point no further amount of ethanol by-product formation could be observed to evolve from the reaction mixture. Upon completion of this step, the spent reaction mixture was allowed to cool to ambient temperatures (ca. 20° C.) on standing overnight for a period of approximately 16 hours. The resulting residual solid was thereafter triturated with petroleum ether and filtered to give 11.53 g (82%) of pure o-[2-ethoxycarbonyl-2-(3-ethoxycarbonylpropionyl)-1-ethylideneamino]anisole. The pure product was characterized by means of mass spectrum (MS) analysis and nuclear magnetic resonance (NMR) data.

後処理

  1. customUpon completion of this step, the spent reaction mixture
  2. customThe resulting residual solid was thereafter triturated with petroleum ether
  3. filtrationfiltered

出典と根拠

ORDレコード
ord-b8da32933a734eab98d21aeccba739b2
出典データセット
uspto-grants-1994_11
特許番号
US05362743

反応ノート

読み込み中…