Реакция #474414

Уравнение реакции

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

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title product

Выход 11.0%

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

Выход 11.0%

Растворители

Acetic acid

Условия реакции

Обработка

1. 1
   ТемператураThe well-stirred suspension was heated
2. 2
   Температураat reflux for 0.5 h
3. 3
   Фильтрацияfiltered through activated charcoal
4. 4
   Другоеevaporated
5. 5
   workup.ADDITIONDichloromethane (50 mL), water (30 mL) and 10% aqueous NaOH (50 mL) were added
6. 6
   ФильтрацияThe suspension was filtered through Perlite
7. 7
   Другоеthe layers were separated
8. 8
   Экстракцияthe aqueous layer was extracted with dichloromethane (2×20 mL)
9. 9
   Промывкаthe combined organic layers were washed with water (10 mL)
10. 10
    Сушкаdried over sodium sulfate
11. 11
    Другоеevaporated
12. 12
    ДругоеThe residue was triturated with chloroform (10 mL)
13. 13
    Другоеthe solid was collected
14. 14
    Промывкаwashed with chloroform (2 mL)

Методика

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)+.

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