Réaction #602749

ord-0db880d49b4548ceaf987917d395acfa

Équation de réaction

O=C1C(=O)C(Cl)=C(Cl)C(Cl)=C1Cl
ortho-chloranil
CCOC(=O)N1C=CC(c2c(-c3ccccc3)nc3ccc(Cl)nn23)C=N1
ethyl 4-[6-chloro-2-phenylimidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate
[Na+].[OH-]
sodium hydroxide
Clc1ccc2nc(-c3ccccc3)c(-c3ccnnc3)n2n1
beige powder
Rendement 71.2%
Clc1ccc2nc(-c3ccccc3)c(-c3ccnnc3)n2n1
6-chloro-2-phenyl-3-(pyridazin-4-yl)imidazo[1,2-b]pyridazine
Rendement 71.2%

Solvants

Conditions de réaction

Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    ExtractionThe product is extracted with chloroform
  2. 2
    SéchageThe organic phase is dried over sodium sulfate
  3. 3
    Concentrationconcentrated under reduced pressure
  4. 4
    AutreThe dark beige residue is crystallized from a mixture of 80 ml of isopropanol and 60 ml of diisopropyl ether under hot conditions

Mode opératoire

22.3 g (58.4 mmol) of ethyl 4-[6-chloro-2-phenylimidazo[1,2-b]pyridazin-3-yl]-4H-pyridazine-1-carboxylate are dissolved in 450 ml of chloroform and 15.1 g (61.3 mmol) of ortho-chloranil are added portionwise. The reaction medium is stirred for 30 minutes at ambient temperature and then poured into a 2N aqueous solution of sodium hydroxide. The product is extracted with chloroform. The organic phase is dried over sodium sulfate and then concentrated under reduced pressure. The dark beige residue is crystallized from a mixture of 80 ml of isopropanol and 60 ml of diisopropyl ether under hot conditions, to give 12.8 g of a beige powder after cooling, isolation by filtration and drying.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US09108971B2uspto-grants-2015_08