Réaction #2286299

Équation de réaction

N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid methyl ester

N-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid methyl ester

sodium hydroxide

→

N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid

Rendement 98.0%

N-[3,5-Dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid

Rendement 98.0%

Solvants

methanol

Conditions de réaction

Traitement

1. 1
   ConcentrationThe solvent was concentrated under vacuum
2. 2
   workup.ADDITIONThe residue was diluted with water (500 mL)
3. 3
   workup.ADDITIONthe mixture was made acidic to pH=1-2 by the addition of a 1N aqueous hydrochloric acid solution
4. 4
   ExtractionThe mixture was extracted with ethyl acetate (2×250 mL)
5. 5
   AutreThe organic layer was separated
6. 6
   Séchagedried with magnesium sulfate
7. 7
   Filtrationfiltered
8. 8
   Concentrationconcentrated
9. 9
   AutreThe resulting solid was dried on high vacuum overnight

Mode opératoire

A suspension of N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid methyl ester (27) (1.87 g, 4.47 mmol) in methanol (35 mL) at 0° C. was treated with a 1N aqueous sodium hydroxide solution (8.95 mL, 8.95 mmol). The reaction mixture was warmed to room temperature and stirred for 2 h. The solvent was concentrated under vacuum. The residue was diluted with water (500 mL), and the mixture was made acidic to pH=1-2 by the addition of a 1N aqueous hydrochloric acid solution. The mixture was extracted with ethyl acetate (2×250 mL). The organic layer was separated, dried with magnesium sulfate, filtered and concentrated. The resulting solid was dried on high vacuum overnight to afford N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid (28) (1.77 g, 98%) as a white solid; EI(+)-HRMS m/z calcd for C15H12Cl3N3O4 (M+H) 403.9966, found 403.9968. Molecular Weight=404.6396; Exact Mass=402.9893

Source