2-Mercaptoethanol → 2-(3-Amino-2-nitro-phenylsulfanyl)-ethanol

HRID 1861108

Reaktionsgleichung

Reaktionsgleichung von HRID 1861108
Cl[C:2]1[C:3]([N+:9]([O-:11])=[O:10])=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].[SH:12][CH2:13][CH2:14][OH:15].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[NH2:5][C:4]1[C:3]([N+:9]([O-:11])=[O:10])=[C:2]([S:12][CH2:13][CH2:14][OH:15])[CH:8]=[CH:7][CH:6]=1

Komponenten

5

Edukt 3

HCID 15672-MercaptoethanolHCID 11430Potassium CarbonateHCID 1010683-Chloro-2-nitroaniline

Produkt 1

HCID 218773312-(3-Amino-2-nitro-phenylsulfanyl)-ethanolAusbeute 93 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel

Reaktionsbedingungen

Temperatur
130 °C

Versuchsvorschrift

3-Chloro-2-nitro-aniline (1.12 g, 6.5 mmol), 2-mercaptoethanol (0.60 ml, 8.6 mmol), and potassium carbonate (0.99 g, 7.1 mmol) were combined in dry DMF (15 ml) and stirred at 130° C. for 4 h. The solution was allowed to cool and was concentrated in vacuo. Purification by silica gel chromatography (70% EtOAc/hexanes) gave 1.29 g (93%) of 2-(3-amino-2-nitro-phenylsulfanyl)-ethanol as a bright red solid. 1H NMR (300 MHz, DMSO-d6) δ 7.20 (t, 1H, J=8.1 Hz), 6.80 (s, 2H), 6.73 (dd, 1H, J=8.4, 0.9 Hz), 6.63 (dd, 1H, J=7.8, 1.2 Hz), 4.92 (t, 1H, J=6.0 Hz), 3.58 (q, 2H, J=6.0 Hz), 2.98 (t, 2H, J=6.0 Hz).

Aufarbeitung

  1. temperatureto cool
  2. concentrationwas concentrated in vacuo
  3. customPurification by silica gel chromatography (70% EtOAc/hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-ff884ce52555403584abc4fc803e3ecc
Quelldatensatz
uspto-grants-2003_03
Patentnummer
US06531491B1

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