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

HRID 1192046Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1192046
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 602073081-[4-Amino-5-(2,4-dichlorophenyl)sulfanyl-2-thienyl]ethanoneAusbeute 99,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23925IronKatalysatorHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

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).

Aufarbeitung

  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

Quellen und Nachweise

ORD-Eintrag
ord-913ec79a6d06446b893fc8fe89f84f74
Quelldatensatz
uspto-grants-2014_03
Patentnummer
US08680139B2

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