反応 #2286338

反応方程式

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

収率 93.0%

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

収率 93.0%

溶媒

acetic acid

2-propanol

反応条件

後処理

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

実験手順

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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