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Sodium Carbonate → HCID 9825929, Verbindung

HRID 272333
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 272333
[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:22])=[C:16]([NH2:21])[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11]2([CH3:24])[CH3:23])=[CH:6][CH:5]=1)([CH3:3])[CH3:2].[C:25](=[O:28])([O-])[O-:26].[Na+].[Na+]>O1CCCC1.[I-].C([N+](CCCC)(CCCC)CCCC)CCC>[CH:1]([C:4]1[CH:9]=[CH:8][C:7]([CH:10]2[C:14]3[C:15]([CH3:22])=[C:16]([N:21]4[CH2:22][C:15]5[CH:16]=[C:17]6[O:26][CH2:25][O:28][C:18]6=[CH:13][C:14]=5[CH2:10]4)[C:17]([CH3:20])=[C:18]([CH3:19])[C:13]=3[O:12][C:11]2([CH3:24])[CH3:23])=[CH:6][CH:5]=1)([CH3:3])[CH3:2]
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

5

Edukt 2

HCID 10340Sodium CarbonateHCID 105199783-(4-Isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine

Produkt 1

HCID 9825929HCID 9825929, VerbindungAusbeute 65,2 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 67553Tetrabutylammonium IodideKatalysatorHCID 8028Tetrahydrofuran
Lösungsmittel

Versuchsvorschrift

To a solution of 3-(4-isopropylphenyl)-2,2,4,6,7-pentamethyl-2,3-dihydro-1-benzofuran-5-amine (835.5 mg, 2.58 mmol) in tetrahydrofuran (20 ml) were added 5,6-bis(chloromethyl)-1,3-benzodioxazole (574.5 mg, 2.62 mmol), sodium carbonate (832.8 mg, 7.88 mmol), and tetrabutylammonium iodide (481.6 mg, 1.30 mmol) and the mixture was refluxed with heating for 23 hours. The reaction mixture was cooled down to room temperature and then poured into ice water. The product was extracted twice with ethyl acetate. The combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate, dried on magnesium sulfate, filtered, and then concentrated under reduced pressure. The residue was crystallized from isopropyl ether to obtain 395.0 mg (33% yield) of the title compound. Melting point: 175-177° C.

Aufarbeitung

  1. temperaturethe mixture was refluxed
  2. temperaturewith heating for 23 hours
  3. extractionThe product was extracted twice with ethyl acetate
  4. washThe combined extracts were washed with an aqueous saturated solution of sodium hydrogen carbonate
  5. customdried on magnesium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe residue was crystallized from isopropyl ether

Quellen und Nachweise

ORD-Eintrag
ord-1aa101ea44334740966fc7f2e4fed867
Quelldatensatz
uspto-grants-2008_11
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US07456162B2

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