2-(3-Amino-2-nitro-phenylsulfanyl)-ethanol → 2-(2,3-Diamino-phenylsulfanyl)-ethanol

HRID 1862149Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1862149
[NH2:1][C:2]1[C:3]([N+:12]([O-])=O)=[C:4]([S:8][CH2:9][CH2:10][OH:11])[CH:5]=[CH:6][CH:7]=1>CCOC(C)=O.[Pd]>[NH2:12][C:3]1[C:2]([NH2:1])=[CH:7][CH:6]=[CH:5][C:4]=1[S:8][CH2:9][CH2:10][OH:11]

Komponenten

4

Edukt 1

HCID 218773312-(3-Amino-2-nitro-phenylsulfanyl)-ethanol

Produkt 1

HCID 190440172-(2,3-Diamino-phenylsulfanyl)-ethanolAusbeute 87 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 23938PalladiumKatalysatorHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

2-(3-Amino-2-nitro-phenylsulfanyl)-ethanol (1.02 g, 4.8 mmol) was reduced by hydrogenation using 45 psi of H2 with 10% Pd—C (180 mg) in EtOAc (25 mL) for 6 h. After filtering through Celite, solvent was removed in vacuo. Purification by silica gel chromatography (EtOAc) gave 762 mg (87%) of 2-(2,3-diamino-phenylsulfanyl)-ethanol as a faintly yellow solid. 1H NMR (300 MHz, CDCl3) δ 6.98 (dd, 1H, J=7.5, 1.5 Hz), 6.60-6.72 (m, 2H), 3.65 (t, 2H, J=5.7 Hz), 3.55 (br s, 5H), 2.91 (t, 2H, J=5.7 Hz).

Aufarbeitung

  1. customfor 6 h
  2. filtrationAfter filtering through Celite, solvent
  3. customwas removed in vacuo
  4. customPurification by silica gel chromatography (EtOAc)

Quellen und Nachweise

ORD-Eintrag
ord-94eff58e540944218540db5f40c171c7
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06534524B1

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