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Sodium Iodide → HCID 19786553, Verbindung

HRID 1646724
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 1646724
Cl[CH2:2][CH2:3][CH2:4][CH:5]1[C:19](=[O:20])[C:9]2[C:10]([C:13]3[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=3)=[N:11][O:12][C:8]=2[CH2:7][CH2:6]1.[CH3:21][C:22]1[NH:23][CH:24]=[CH:25][N:26]=1.C(N(C(C)C)CC)(C)C.[I-].[Na+]>CN(C)C=O>[CH3:21][C:22]1[N:23]([CH2:2][CH2:3][CH2:4][CH:5]2[C:19](=[O:20])[C:9]3[C:10]([C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)=[N:11][O:12][C:8]=3[CH2:7][CH2:6]2)[CH:24]=[CH:25][N:26]=1
KomponentenReaktionsbedingungenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

6

Edukt 4

HCID 5238Sodium IodideHCID 127492-MethylimidazoleHCID 81531DiisopropylethylamineHCID 19786584HCID 19786584, Verbindung

Produkt 1

HCID 19786553HCID 19786553, VerbindungAusbeute 40,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228
Dimethylformamide
Lösungsmittel

Reaktionsbedingungen

Temperatur
76 °C

Versuchsvorschrift

To a solution consisting of 5-(3-chloropropyl)-6,7-dihydro-3-phenyl-1,2-benzisoxazol-4(5H)-one (5.80 g) and dimethylformamide (57.0 ml) was added 2-methylimidazole (3.30 g), diisopropylethyl amine (10.5 ml) and sodium iodide (9.04 g) at room temperature with stirring. The reaction was flushed with nitrogen and warmed at 76° C. for 1 hour. Upon cooling to room temperature, dilute aqueous sodium bicarbonate and ethyl acetate were added to the reaction mixture. The layers were separated and the aqueous layer extracted twice with ethyl acetate and once with ether. The combined organic layers were washed with brine and concentrated to give the crude product. Drying was accomplished by azeotroping with benzene. Purification via flash column chromatography (silica gel, 2% triethylamine/0-20% methanol/ether) afforded 2.70 g (40%) of 6,7-dihydro-5-[3-(2-methyl-1H-imidazol-1-yl)-propyl]-3-phenyl-1,2-benzisoxazol-4(5H)-one. Recrystallization from dichloromethane/ether/pentane gave the product, m.p. 97°-99° C.

Aufarbeitung

  1. customThe reaction was flushed with nitrogen
  2. temperatureUpon cooling to room temperature
  3. additiondilute aqueous sodium bicarbonate and ethyl acetate were added to the reaction mixture
  4. customThe layers were separated
  5. extractionthe aqueous layer extracted twice with ethyl acetate and once with ether
  6. washThe combined organic layers were washed with brine
  7. concentrationconcentrated
  8. customto give the crude product
  9. customDrying
  10. customby azeotroping with benzene
  11. customPurification via flash column chromatography (silica gel, 2% triethylamine/0-20% methanol/ether)

Quellen und Nachweise

ORD-Eintrag
ord-08e0b853f72e48bcb7ee833d18be5c24
Quelldatensatz
uspto-grants-1993_01
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05180834

Notizen zur Reaktion

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