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

HRID 1192046노트

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HRID 1192046 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 23925Iron촉매HCID 962Water용매

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온도
80 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-913ec79a6d06446b893fc8fe89f84f74
출처 데이터셋
uspto-grants-2014_03
특허 번호
US08680139B2

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