Diethyl acetylenedicarboxylate → 2-[2-Chloro-5-(methoxycarbonyl)phenylamino]-2-butenedioic acid diethyl ester

HRID 272562

反応式

HRID 272562 の反応式
[Cl:1][C:2]1[CH:11]=[CH:10][C:5]([C:6]([O:8][CH3:9])=[O:7])=[CH:4][C:3]=1[NH2:12].[CH2:13]([O:15][C:16](=[O:24])[C:17]#[C:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:14]>C(O)C>[CH2:13]([O:15][C:16](=[O:24])[C:17]([NH:12][C:3]1[CH:4]=[C:5]([C:6]([O:8][CH3:9])=[O:7])[CH:10]=[CH:11][C:2]=1[Cl:1])=[CH:18][C:19]([O:21][CH2:22][CH3:23])=[O:20])[CH3:14]

参加物

4

反応物 2

HCID 69803Diethyl acetylenedicarboxylateHCID 593055Methyl 3-Amino-4-chlorobenzoate

生成物 1

HCID 589597002-[2-Chloro-5-(methoxycarbonyl)phenylamino]-2-butenedioic acid diethyl ester

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

To a solution of 22 (5.00 g, 26.9 mmol) in ethanol (50 mL) was added but-2-ynedioic acid diethyl ester (5.02 g, 29.5 mmol) at room temperature. The reaction mixture was heated at 90° C. for 18 h and then cooled to room temperature. The solvent was removed under reduced pressure. The crude residue was washed with a solution of 1:1 Hexanes/diethyl ether (100 mL) to afford a white solid (23, 9.08 g, 95.1%). 1H NMR (DMSO-d6, 300 MHz) δ ?9.80 (s, 1H), 7.65-7.66 (m, 2H), 7.38 (s, 1H), 5.54 (s, 1H), 4.13-4.22 (m, 4H), 3.83 (s, 3H), 1.22 (t, J=7.1 Hz, 3H), 1.11 (t, J=7.1 Hz, 3H).

後処理

  1. temperaturecooled to room temperature
  2. customThe solvent was removed under reduced pressure
  3. washThe crude residue was washed with a solution of 1:1 Hexanes/diethyl ether (100 mL)
  4. customto afford a white solid (23, 9.08 g, 95.1%)

出典と根拠

ORDレコード
ord-816b1824191c4f5ca31244319dbfbb57
出典データセット
uspto-grants-2008_11
特許番号
US07456178B2

関連ノート

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