Reaktion #2286300

Reaktionsgleichung

sodium acetate

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

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

→

N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-oxalamic acid

Ausbeute 56.1%

N-[3,5-Dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-oxalamic acid

Ausbeute 56.1%

Lösungsmittel

acetic acid

Reaktionsbedingungen

Aufarbeitung

1. 1
   TemperaturThe reaction mixture was cooled to room temperature
2. 2
   Einengenwas concentrated under vacuum
3. 3
   workup.ADDITIONThe resulting solid was diluted with water (50 mL)
4. 4
   workup.ADDITIONThe mixture was made acidic to pH=3 by the addition of glacial acetic acid
5. 5
   FiltrationThe solids were filtered
6. 6
   Waschenrinsed well with water
7. 7
   Sonstigedried on the funnel
8. 8
   Temperaturmethyl tert-butyl ether: hexanes (3 mL) and then was heated to reflux
9. 9
   TemperaturThe mixture was cooled
10. 10
    Filtrationfiltered
11. 11
    Filtrationfiltered
12. 12
    SonstigeThe resulting pure solid was dried under high vacuum for 24 h
13. 13
    Sonstigedried in a vacuum oven at 80° C. for 24 h

Vorschrift

A mixture of glacial acetic acid (55 mL), sodium acetate (1.2 g, 14.7 mmol) and N-[3,5-dichloro-4-(6-chloro-5-isopropyl-pyridazin-3-yloxy)-phenyl]-oxalamic acid (28) (1.7 g, 4.2 mmol) was heated to 100° C. for 24 h. The reaction mixture was cooled to room temperature and was concentrated under vacuum. The resulting solid was diluted with water (50 mL). The mixture was made acidic to pH=3 by the addition of glacial acetic acid. The solids were filtered and rinsed well with water and dried on the funnel. The solid was slurried in 1:1:2 isopropyl acetate: methyl tert-butyl ether: hexanes (3 mL) and then was heated to reflux. The mixture was cooled and filtered. A slight amount of impurity was detected by TLC. The solid was slurried in isopropyl acetate (10 mL) and filtered. The resulting pure solid was dried under high vacuum for 24 h and then dried in a vacuum oven at 80° C. for 24 h to afford N-[3,5-dichloro-4-(5-isopropyl-6-oxo-1,6-dihydro-pyridazin-3-yloxy)-phenyl]-oxalamic acid (29) (0.91 g, 56%) as a white solid; EI(+)-HRMS m/z calcd for C15H13Cl2N3O5 (M+H) 386.0305, found 386.0308. Molecular Weight=386.1940; Exact Mass=385.0232

Quelle