反应 #2286338

反应方程式

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

收率 93.0%

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

收率 93.0%

溶剂

acetic acid

2-propanol

反应条件

后处理

1. 1
   温度The resulting mixture was heated to 95° C. for 2 h
2. 2
   过滤At this time, the reaction was filtered hot through a pad of celite
3. 3
   洗涤was washed with water and ethyl acetate
4. 4
   浓缩The filtrates were concentrated
5. 5
   其他to remove the majority of organics
6. 6
   workup.ADDITIONThe remaining solution was diluted with water (500 mL)
7. 7
   萃取The solution was extracted with ethyl acetate (3×200 mL)
8. 8
   干燥The combined organics were dried with magnesium sulfate
9. 9
   过滤filtered
10. 10
    浓缩concentrated under vacuum
11. 11
    温度was cooled in the freezer for 30 min
12. 12
    其他The solid that formed
13. 13
    过滤was collected by filtration
14. 14
    洗涤was washed with cold diethyl ether

实验过程

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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