Ethanol → 4-Amino-2-methylbenzene-1-thiol

HRID 856760Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 856760
[CH3:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[SH:11].C(O)C>C(O)(=O)C>[NH2:8][C:6]1[CH:5]=[CH:4][C:3]([SH:11])=[C:2]([CH3:1])[CH:7]=1

Komponenten

4

Edukt 2

HCID 702EthanolHCID 107734502-Methyl-4-nitrobenzenethiol

Produkt 1

HCID 198673854-Amino-2-methylbenzene-1-thiolAusbeute 31,3 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

To a solution of 2-methyl-4-nitrothiophenol (7.0 g) in acetic acid (100 ml) was added reduced iron (21.0 g) and the mixture was stirred for 40 hours. Ethanol was added to the mixture, and the insolubles were filtered off, and the solvent was distilled off under reduced pressure. To the obtained residue was added water, and the solution was neutralized with an aqueous solution of saturated sodium bicarbonate, and extracted with ethyl acetate. The organic layer was dried over magnesium sulfate and the solvent was distilled off under reduced pressure. The obtained residue was separated and purified by silica gel column chromatography (hexane-ethyl acetate=3:1→hexane:ethyl acetate=0.2:1), to give 4-amino-2-methylthiophenol (1.8 g).

Aufarbeitung

  1. filtrationthe insolubles were filtered off
  2. distillationthe solvent was distilled off under reduced pressure
  3. additionTo the obtained residue was added water
  4. extractionextracted with ethyl acetate
  5. dry with materialThe organic layer was dried over magnesium sulfate
  6. distillationthe solvent was distilled off under reduced pressure
  7. customThe obtained residue was separated
  8. custompurified by silica gel column chromatography (hexane-ethyl acetate=3:1→hexane:ethyl acetate=0.2:1)

Quellen und Nachweise

ORD-Eintrag
ord-88180d6cae5445b78e6629bc4fc625e5
Quelldatensatz
uspto-grants-2007_08
Patentnummer
US07262185B2

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