Diethyl (ethoxymethylene)malonate → Diethyl 2-((4-bromophenylamino)methylene)malonate

HRID 852980ノート

反応式

HRID 852980 の反応式
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19]OCC)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]>C(O)C>[CH2:9]([O:11][C:12](=[O:23])[C:13](=[CH:19][NH:6][C:5]1[CH:7]=[CH:8][C:2]([Br:1])=[CH:3][CH:4]=1)[C:14]([O:16][CH2:17][CH3:18])=[O:15])[CH3:10]

参加物

4

反応物 2

HCID 6871Diethyl (ethoxymethylene)malonateHCID 78074-Bromoaniline

生成物 1

HCID 1591151Diethyl 2-((4-bromophenylamino)methylene)malonate収率 87.1%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
90 °C

実験手順

A mixture of 4-bromoaniline (100 g, 563.9 mmol) and 2-ethoxymethylene-malonic acid diethyl ester (126.9 g, 575 mmol) was heated to 90° C. Then, the resulting brown mixture was stirred for 5 h. After cooling to room temperature, the reaction mixture was diluted with ethanol (˜200 mL) and cooled down in an ice-water bath to afford a hard solid. This mixture was then heated to break down the hard solid and also to remove most of the impurities. After cooling the suspension in the refrigerator, the solids were collected by filtration and washed with cold ethanol. After drying in air, 168 g (87% yield) of 2-[(4-bromo-phenylamino)-methylene]-malonic acid diethyl ester was isolated as a white solid: mp 100-102° C. (lit. 100-101° C.).

後処理

  1. temperatureAfter cooling to room temperature
  2. temperaturecooled down in an ice-water bath
  3. customto afford a hard solid
  4. temperatureThis mixture was then heated
  5. customalso to remove most of the impurities
  6. temperatureAfter cooling the suspension in the refrigerator
  7. filtrationthe solids were collected by filtration
  8. washwashed with cold ethanol
  9. customAfter drying in air

出典と根拠

ORDレコード
ord-e0720eccc841487daf6259ef0aea610e
出典データセット
uspto-grants-2007_08
特許番号
US07253285B2

反応ノート

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