Реакция #2286338

Уравнение реакции

dimethyl-thiocarbamic acid S-(2,6-dichloro-4-nitro-phenyl)ester

Dimethyl-thiocarbamic acid S-(2,6-dichloro-4-nitro-phenyl)ester

water

→

dimethyl-thiocarbamic acid S-(4-amino-2,6-dichloro-phenyl)ester

Выход 93.0%

Dimethyl-thiocarbamic acid S-(4-amino-2,6-dichloro-phenyl)ester

Выход 93.0%

Растворители

acetic acid

2-propanol

Условия реакции

Обработка

1. 1
   ТемператураThe resulting mixture was heated to 95° C. for 2 h
2. 2
   ФильтрацияAt this time, the reaction was filtered hot through a pad of celite
3. 3
   Промывкаwas washed with water and ethyl acetate
4. 4
   КонцентрированиеThe filtrates were concentrated
5. 5
   Другоеto remove the majority of organics
6. 6
   workup.ADDITIONThe remaining solution was diluted with water (500 mL)
7. 7
   ЭкстракцияThe solution was extracted with ethyl acetate (3×200 mL)
8. 8
   СушкаThe combined organics were dried with magnesium sulfate
9. 9
   Фильтрацияfiltered
10. 10
    Концентрированиеconcentrated under vacuum
11. 11
    Температураwas cooled in the freezer for 30 min
12. 12
    ДругоеThe solid that formed
13. 13
    Фильтрацияwas collected by filtration
14. 14
    Промывкаwas washed with cold diethyl ether

Методика

A mixture of dimethyl-thiocarbamic acid S-(2,6-dichloro-4-nitro-phenyl)ester (80) (1.6 g, 5.4 mmol) in glacial acetic acid (24 mL), 2-propanol (48 mL), and water (24 mL) heated to 50° C. was treated with iron powder (2.1 g, 37.8 mmol). The resulting mixture was heated to 95° C. for 2 h. At this time, the reaction was filtered hot through a pad of celite and was washed with water and ethyl acetate. The filtrates were concentrated to remove the majority of organics. The remaining solution was diluted with water (500 mL) and was then brought to pH=8 with a concentrated ammonium hydroxide solution. The solution was extracted with ethyl acetate (3×200 mL). The combined organics were dried with magnesium sulfate, filtered and concentrated under vacuum. The resulting residue was slurried with diethyl ether and was cooled in the freezer for 30 min. The solid that formed was collected by filtration and was washed with cold diethyl ether to afford dimethyl-thiocarbamic acid S-(4-amino-2,6-dichloro-phenyl)ester (81) (1.33 g, 93%) as a white solid; EI(+)-HRMS m/e calcd for C9H10Cl2N2OS (M+H)+ 264.9964, found 264.9964. Exact Mass=263.9891; Molecular weight=265.16

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