Reaction #2286334

Reaction equation

2-(3,5-dichloro-4-mercapto-phenyl)-ethanol

2-(3,5-Dichloro-4-mercapto-phenyl)-ethanol

3,6-dichloro-4-isopropyl-pyridazine

3,6-dichloro-4-isopropyl pyridazine

potassium carbonate

hydrochloric acid

→

2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-ethanol

Yield 52.4%

2-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-ethanol

Yield 52.4%

Solvents

water

dimethyl sulfoxide

Conditions

Workup

1. 1
   TemperatureAt this time, the reaction was cooled to 25° C.
2. 2
   ExtractionThe mixture was extracted with ethyl acetate (2×200 mL)
3. 3
   WashThe organics were then washed with water (1×100 mL)
4. 4
   Dryinga saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under vacuum

Procedure

A solution of 2-(3,5-dichloro-4-mercapto-phenyl)-ethanol (73) (620 mg, 2.78 mmol) in dimethyl sulfoxide (25 mL) was treated with 3,6-dichloro-4-isopropyl-pyridazine (7) (530 mg, 2.78 mmol) and potassium carbonate (1.54 g, 11.12). The resulting mixture was heated to 90° C. for 18 h. At this time, the reaction was cooled to 25° C., poured into a solution of water (200 mL) and a 1N aqueous hydrochloric acid solution (25 mL). The mixture was extracted with ethyl acetate (2×200 mL). The organics were then washed with water (1×100 mL) and a saturated aqueous sodium chloride solution (1×100 mL), dried with magnesium sulfate, filtered, and concentrated under vacuum. Flash chromatography (Merck Silica gel 60, 230-400 mesh, 70:30 petroleum ether/ethyl acetate) afforded 2-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-ylsulfanyl)-phenyl]-ethanol (74) (550 mg, 52%) as a pale yellow oil; EI(+)-HRMS m/e calcd for C15H15Cl3N2OS (M+H)+ 377.0044, found 377.0043. Exact Mass=375.9971; Molecular weight=377.72

Source