反応 #2286339

反応方程式

hydrochloric acid

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

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

potassium hydroxide

→

4-amino-2,6-dichloro-benzenethiol

収率 69.0%

4-Amino-2,6-dichloro-benzenethiol

収率 69.0%

溶媒

water

ethanol

反応条件

後処理

1. 1
   温度At this time, the reaction was cooled to 25° C.
2. 2
   抽出was extracted with ethyl acetate (2×250 mL)
3. 3
   乾燥The organics were dried with magnesium sulfate
4. 4
   ろ過filtered
5. 5
   濃縮concentrated under vacuum to an orange solid
6. 6
   ろ過collected by filtration
7. 7
   洗浄washed with chloroform
8. 8
   濃縮The filtrate was concentrated under vacuum
9. 9
   その他purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 85:15 petroleum ether/ethyl acetate)

実験手順

A solution of dimethyl-thiocarbamic acid S-(4-amino-2,6-dichloro-phenyl)ester (81) (2.0 g, 7.5 mmol) in ethanol was treated with a 3N aqueous potassium hydroxide solution. The reaction was heated to 95° C. for 2 d. At this time, the reaction was cooled to 25° C. and was then acidified to pH=2 with a 3N aqueous hydrochloric acid solution. This solution was diluted with water (500 mL) and then was extracted with ethyl acetate (2×250 mL). The organics were dried with magnesium sulfate, filtered, and concentrated under vacuum to an orange solid. The solid was slurried in chloroform, collected by filtration and washed with chloroform. The filtrate was concentrated under vacuum and purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 85:15 petroleum ether/ethyl acetate) to afford 4-amino-2,6-dichloro-benzenethiol (82) (1.0 g, 69%) as a white solid; EI(+)-HRMS m/e calcd for C6H5Cl2NS (M+) 192.9520, found 192.9519. Exact Mass=192.9520; Molecular weight=194.08

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