Réaction #2286300

Équation de réaction

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

Rendement 56.1%

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

Rendement 56.1%

Solvants

acetic acid

Conditions de réaction

Traitement

1. 1
   TempératureThe reaction mixture was cooled to room temperature
2. 2
   Concentrationwas 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
   Lavagerinsed well with water
7. 7
   Autredried on the funnel
8. 8
   Températuremethyl tert-butyl ether: hexanes (3 mL) and then was heated to reflux
9. 9
   TempératureThe mixture was cooled
10. 10
    Filtrationfiltered
11. 11
    Filtrationfiltered
12. 12
    AutreThe resulting pure solid was dried under high vacuum for 24 h
13. 13
    Autredried in a vacuum oven at 80° C. for 24 h

Mode opératoire

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

Source