Ethanol → 1-[4-Amino-5-(2,4-dichlorophenyl)sulfanyl-2-thienyl]ethanone

HRID 1192046ノート

反応式

HRID 1192046 の反応式
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[S:9][C:10]1[S:14][C:13]([C:15](=[O:17])[CH3:16])=[CH:12][C:11]=1[N+:18]([O-])=O.C(O)C.[Cl-].[NH4+]>[Fe].O>[NH2:18][C:11]1[CH:12]=[C:13]([C:15](=[O:17])[CH3:16])[S:14][C:10]=1[S:9][C:3]1[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=1[Cl:1]

参加物

6

反応物 3

HCID 702EthanolHCID 25517Ammonium ChlorideHCID 469319521-[5-(2,4-Dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone

生成物 1

HCID 602073081-[4-Amino-5-(2,4-dichlorophenyl)sulfanyl-2-thienyl]ethanone収率 99.6%

試薬・触媒・溶媒 2

HCID 23925Iron触媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

To a two necked 250 mL round bottom flask, charged with 1-[5-(2,4-Dichlorophenylsulfanyl)-4-nitro-2-thienyl]ethanone (7.0 g, 20.2 mmol) prepared as in example 2, 50 mL ethanol and 50 mL of water followed by ammonium chloride (4.32 g, 80.8 mmol) and iron powder (4.53 g, 80.8 mmol). The resulting reaction mixture was heated at 80° C. for 2 hours. After this time, the reaction mixture was cooled to ambient temperature and was passed through a cellite cartridge. The filtrate was concentrated and water was added to the residue and extracted with ethyl acetate. The combined organic layer was separated, dried (Na2SO4), filtered and concentrated to afford the title product (6.4 g, 78% yield). 1H NMR (400 MHz, d6-DMSO) δ: 7.64 (1H, s), 7.44 (1H, s), 7.37 (1H, m), 6.68 (1H, m), 2.50 (3H, s).

後処理

  1. customThe resulting reaction mixture
  2. temperatureAfter this time, the reaction mixture was cooled to ambient temperature
  3. concentrationThe filtrate was concentrated
  4. additionwater was added to the residue
  5. extractionextracted with ethyl acetate
  6. customThe combined organic layer was separated
  7. dry with materialdried (Na2SO4)
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-913ec79a6d06446b893fc8fe89f84f74
出典データセット
uspto-grants-2014_03
特許番号
US08680139B2

反応ノート

読み込み中…