Réaction #1244450

Équation de réaction

N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamide

N-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamide

sodium hydroxide

→

6-(4-amino-2,6-dichloro-phenylsulfanyl)-4-isopropyl-2H-pyridazin-3-one

Rendement 99.1%

6-(4-Amino-2,6-dichloro-phenylsulfanyl)-4-isopropyl-2H-pyridazin-3-one

Rendement 99.1%

Solvants

methanol

water

water

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction was then heated
2. 2
   Températureto reflux for 18 h
3. 3
   Extractionextracted with ethyl acetate (3×300 mL)
4. 4
   LavageThe organics were washed with a saturated aqueous sodium chloride solution (1×200 mL)
5. 5
   Séchagedried with magnesium sulfate
6. 6
   Filtrationfiltered
7. 7
   Concentrationconcentrated under vacuum

Mode opératoire

A mixture of N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-ylsulfanyl)-phenyl]-acetamide (84) (4.0 g, 10.7 mmol) in methanol (15 mL) and water (15 mL) was treated with powdered sodium hydroxide (2.14 g, 53.5 mmol). The reaction was then heated to reflux for 18 h. At this time, the reaction was cooled to 25° C., diluted with water (500 mL) and extracted with ethyl acetate (3×300 mL). The organics were washed with a saturated aqueous sodium chloride solution (1×200 mL), dried with magnesium sulfate, filtered and concentrated under vacuum to afford 6-(4-amino-2,6-dichloro-phenylsulfanyl)-4-isopropyl-2H-pyridazin-3-one (85) (3.5 g, 99%) as a light tan solid. The material was used without further purification; ES(+)-HRMS m/e calcd for C13H13Cl2N3OS (M+H)+ 330.0229, found 330.0229. Exact Mass=329.0156; Molecular weight=330.24

Source