تفاعل #2286339

معادلة التفاعل

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

المردود 69.0%

4-Amino-2,6-dichloro-benzenethiol

المردود 69.0%

المذيبات

water

ethanol

ظروف التفاعل

المعالجة

1. 1
   درجة الحرارةAt this time, the reaction was cooled to 25° C.
2. 2
   استخلاصwas extracted with ethyl acetate (2×250 mL)
3. 3
   تجفيفThe organics were dried with magnesium sulfate
4. 4
   ترشيحfiltered
5. 5
   تركيزconcentrated under vacuum to an orange solid
6. 6
   ترشيحcollected by filtration
7. 7
   غسيلwashed with chloroform
8. 8
   تركيزThe filtrate was concentrated under vacuum
9. 9
   أخرىpurified by flash chromatography (Merck Silica gel 60, 230-400 mesh, 85:15 petroleum ether/ethyl acetate)

الإجراء التجريبي

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

المصدر