Reaction #2286340

Reaction equation

4-amino-2,6-dichloro-benzenethiol

4-Amino-2,6-dichloro-benzenethiol

3,6-dichloro-4-isopropyl-pyridazine

3,6-dichloro-4-isopropyl pyridazine

potassium carbonate

hydrochloric acid

hydrochloric acid

→

3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenylamine

Yield 72.0%

3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenylamine

Yield 72.0%

Solvents

N,N-dimethylformamide

Conditions

Workup

1. 1
   TemperatureAt this time, the reaction was cooled to 25° C.
2. 2
   Extractionwas extracted with ethyl acetate (2×100 mL)
3. 3
   WashThe organics were washed with a saturated aqueous sodium chloride solution (1×50 mL)
4. 4
   Dryingdried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under vacuum

Procedure

A solution of 4-amino-2,6-dichloro-benzenethiol (82) (1.0 g, 5.2 mmol) in N,N-dimethylformamide at 25° C. was treated with 3,6-dichloro-4-isopropyl-pyridazine (7) (990 mg, 5.2 mmol) and potassium carbonate (2.16 g, 15.6 mmol). The resulting mixture was heated to 90° C. for 18 h. At this time, the reaction was cooled to 25° C., poured onto a mixture of ice water and a 1N aqueous hydrochloric acid solution (10 mL). The resulting solution was brought to pH=7 with additional 1N aqueous hydrochloric acid solution and then was extracted with ethyl acetate (2×100 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×50 mL), dried with magnesium sulfate, filtered and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 80/20 petroleum ether/ethyl acetate) afforded 3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenylamine (83) (1.29 g, 72%) as an off-white foam; ES(+)-HRMS m/e calcd for C13H12Cl3N3S (M+H)+ 347.9891, found 347.9889. Exact Mass=346.9817; Molecular weight=348.68

Source