Methanol → N-[4-(1,3-dioxolyl)phenyl]isatin

HRID 277348

Reaktionsgleichung

Reaktionsgleichung von HRID 277348
[NH:1]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:4](=[O:5])[C:2]1=[O:3].[H-].[Na+].[CH3:14][OH:15]>CN(C=O)C.C(Cl)(Cl)Cl.[Cu]I>[O:15]1[CH:4]=[CH:2][O:3][CH:14]1[C:6]1[CH:11]=[CH:10][C:9]([N:1]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:4](=[O:5])[C:2]2=[O:3])=[CH:8][CH:7]=1

Komponenten

7

Edukt 3

HCID 887MethanolHCID 7054IsatinHCID 24758Sodium hydride

Produkt 1

HCID 22016430N-[4-(1,3-dioxolyl)phenyl]isatin

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)KatalysatorHCID 6212ChloroformLösungsmittel2×HCID 6228DimethylformamideLösungsmittel

Versuchsvorschrift

Isatin (1.88 g, 0.0128 mol) in anhydrous DMF (100 mL) was cooled in an ice-bath under nitrogen and treated with sodium hydride (0.3 g, 1 equivalent). The reaction was warmed to room temperature and stirred for 1 hour. It was then treated with 2-(4-bromophenyl)-1,3-dioxalane (2.83 g, 0.0124 mol) followed by CuI (4.71 g, 2 equivalents). This suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours. It was then cooled to room temperature and diluted with an equal volume of chloroform. The resulting suspension was filtered and the filtrate was concentrated under reduced pressure. The residue was suspended in xylenes (100 mL) and evaporated to dryness. A thick, viscous oil was recovered which was used as such for the next reaction. TLC (5% methanol in chloroform) showed clean conversion, Rf (product)=0.91.

Aufarbeitung

  1. temperatureThis suspension was heated in an oil-bath at 135° C. under nitrogen for 16 hours
  2. temperatureIt was then cooled to room temperature
  3. filtrationThe resulting suspension was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customevaporated to dryness
  6. customA thick, viscous oil was recovered which
  7. customsuch for the next reaction

Quellen und Nachweise

ORD-Eintrag
ord-c51df4dc831148f48ec79beb81115583
Quelldatensatz
uspto-grants-2002_03
Patentnummer
US06355803B1

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