Réaction #992718

ord-9374108a7280443e8dba6ab2123f1ac4

Équation de réaction

CC(=O)Nc1ccc2c(c1)Oc1ccc(NC(C)=O)cc1O2
2,7-bis(acetylamino)dibenzodioxin
Ic1ccccc1
iodobenzene
O=C([O-])[O-].[K+].[K+]
potassium carbonate
c1ccc2ncccc2c1
quinoline
O=C(Cc1ccccc1)Nc1ccc2c(c1)Oc1ccc(NC(=O)Cc3ccccc3)cc1O2
crude product
O=C(Cc1ccccc1)Nc1ccc2c(c1)Oc1ccc(NC(=O)Cc3ccccc3)cc1O2
2,7-bis(N-phenylacetylamino)dibenzodioxin

Conditions de réaction

Température
170°CELSIUS
Conditions détaillées
See reaction.notes.procedure_details.

Traitement

  1. 1
    Températurewas heated
  2. 2
    TempératureThe reaction mixture was cooled to room temperature
  3. 3
    Autrea precipitate was separated by filtration
  4. 4
    workup.ADDITIONTo the filtrate was added 500 ml of water
  5. 5
    Autrethe organic layer was separated from the aqueous layer
  6. 6
    ConcentrationThe organic layer was concentrated
  7. 7
    Autredried under reduced pressure

Mode opératoire

A slurry prepared from 34.3 g (0.115 mole) of 2,7-bis(acetylamino)dibenzodioxin, 96.4 g (0.576 mole) of iodobenzene, 48.2 g (0.253 mole) of copper (I) iodide, 63.6 g (0.460 mole) of potassium carbonate, and 1500 ml of quinoline was heated with stirring at 170° C. for 48 hours. The reaction mixture was cooled to room temperature, 500 ml of methylene chloride and 500 ml of water were added, and a precipitate was separated by filtration. To the filtrate was added 500 ml of water and the organic layer was separated from the aqueous layer. The organic layer was concentrated and dried under reduced pressure to give 79.4 g of a crude product which was used without purification in the next reaction.

Source

DOI: 10.6084/m9.figshare.5104873.v1Brevet: US08012606B2uspto-grants-2011_09