Nitromethane → (E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine

HRID 872447

反応式

HRID 872447 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12]([CH:13]=O)=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8].[N+:16]([CH3:19])([O-])=O.C([O-])(=O)C.[NH4+]>C(O)(=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([C:9]2[O:15][C:12](/[CH:13]=[CH:19]/[NH2:16])=[CH:11][CH:10]=2)[CH:5]=[CH:6][C:7]=1[Cl:8]

参加物

5

反応物 3

HCID 6375NitromethaneHCID 517165Ammonium AcetateHCID 6176885-(3,4-Dichlorophenyl)-2-furaldehyde

生成物 1

HCID 67170044(E)-2-(5-(3,4-dichlorophenyl)furan-2-yl)ethenamine収率 92.5%

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
80 °C

実験手順

To a stirred solution of 5-(3,4-dichlorophenyl)furfural (1.18 g, 4.89 mmol) in acetic acid (30 ml) was added nitromethane (0.535 ml, 9.78 mmol) and ammonium acetate (1.13 g, 14.7 mmol). The reaction mixture was heated at 80° C. for 4.5 h. Cooled reaction mixture was poured onto ice water (30 ml) and thus formed precipitate was filtered, washed with water and dried under vacuum to give 1.15 g (83%) of the title compound. 1H-NMR (400 MHz; d6-DMSO): δ 7.37 (d, 1H), 7.43 (d, 1H), 7.76 (d, 1H), 7.95 (dd, 1H), 8.03 (d, 1H), 8.19 (d, 1H), 8.31 (d, 1H).

後処理

  1. temperatureCooled
  2. customreaction mixture
  3. additionwas poured onto ice water (30 ml) and thus formed precipitate
  4. filtrationwas filtered
  5. washwashed with water
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-d3ec8c8042a2450380a5863f5cd8d24d
出典データセット
uspto-grants-2015_03
特許番号
US08975254B2

関連ノート

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