반응 #2286339

반응 방정식

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

수율 69.0%

4-Amino-2,6-dichloro-benzenethiol

수율 69.0%

용매

water

ethanol

반응 조건

후처리

1. 1
   온도At this time, the reaction was cooled to 25° C.
2. 2
   추출was extracted with ethyl acetate (2×250 mL)
3. 3
   건조The organics were dried with magnesium sulfate
4. 4
   여과filtered
5. 5
   농축concentrated under vacuum to an orange solid
6. 6
   여과collected by filtration
7. 7
   세척washed with chloroform
8. 8
   농축The filtrate was concentrated under vacuum
9. 9
   기타purified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 85:15 petroleum ether/ethyl acetate)

실험 절차

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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