Reaktion #474414

Reaktionsgleichung

[2-nitro-1-(4-nitrophenyl)-ethylsulfanyl]-acetic acid methyl ester

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title product

Ausbeute 11.0%

6-(4-aminophenyl)-thiomorpholin-3-one

Ausbeute 11.0%

Lösungsmittel

Acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe well-stirred suspension was heated
2. 2
   Temperaturat reflux for 0.5 h
3. 3
   Filtrationfiltered through activated charcoal
4. 4
   Sonstigeevaporated
5. 5
   workup.ADDITIONDichloromethane (50 mL), water (30 mL) and 10% aqueous NaOH (50 mL) were added
6. 6
   FiltrationThe suspension was filtered through Perlite
7. 7
   Sonstigethe layers were separated
8. 8
   Extraktionthe aqueous layer was extracted with dichloromethane (2×20 mL)
9. 9
   Waschenthe combined organic layers were washed with water (10 mL)
10. 10
    Trocknendried over sodium sulfate
11. 11
    Sonstigeevaporated
12. 12
    SonstigeThe residue was triturated with chloroform (10 mL)
13. 13
    Sonstigethe solid was collected
14. 14
    Waschenwashed with chloroform (2 mL)

Vorschrift

Acetic acid (240 mL) was heated to 72° C., then Zn (25.38 g, 388 mmol) and [2-nitro-1-(4-nitrophenyl)-ethylsulfanyl]-acetic acid methyl ester (3.00 g, 10.00 mmol) were added in one portion. The well-stirred suspension was heated at reflux for 0.5 h, filtered through activated charcoal and evaporated. Dichloromethane (50 mL), water (30 mL) and 10% aqueous NaOH (50 mL) were added. The suspension was filtered through Perlite, the layers were separated and the aqueous layer was extracted with dichloromethane (2×20 mL). the combined organic layers were washed with water (10 mL), dried over sodium sulfate and evaporated. The residue was triturated with chloroform (10 mL) and the solid was collected and washed with chloroform (2 mL) to obtain the title product (0.225 g, 1.08 mmol, 11%). ESMS m/z 209 (M+H)+.

Quelle