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Sodium Iodide → 4-[(1,3-dioxoisoindol-2-yl)methyl]-N-(2-methoxyphenyl)benzamide

HRID 2452
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 2452
[C:1]1(=[O:11])[NH:5][C:4](=[O:6])[C:3]2=[CH:7][CH:8]=[CH:9][CH:10]=[C:2]12.[H-].[Na+].Cl[CH2:15][C:16]1[CH:32]=[CH:31][C:19]([C:20]([NH:22][C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][C:24]=2[O:29][CH3:30])=[O:21])=[CH:18][CH:17]=1.[I-].[Na+]>C1COCC1.CN(C=O)C>[CH3:30][O:29][C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][C:23]=1[NH:22][C:20](=[O:21])[C:19]1[CH:18]=[CH:17][C:16]([CH2:15][N:5]2[C:1](=[O:11])[C:2]3=[CH:10][CH:9]=[CH:8][CH:7]=[C:3]3[C:4]2=[O:6])=[CH:32][CH:31]=1
KomponentenVersuchsvorschriftAufarbeitungQuellen und NachweiseNotizen zur Reaktion

Komponenten

7

Edukt 4

HCID 5238Sodium IodideHCID 6809PhthalimideHCID 24758Sodium hydrideHCID 196899684-Chloromethyl-N-(2-methoxyphenyl)benzamide

Produkt 1

HCID 29945204-[(1,3-dioxoisoindol-2-yl)methyl]-N-(2-methoxyphenyl)benzamideAusbeute 77,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228
Dimethylformamide
Lösungsmittel
HCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

In an atmosphere of argon, phthalimide (150 mg, 1.0 mmol) was dissolved in THF (10 ml) to which was subsequently added sodium hydride (44 mg, 60%, 1.1 mmol) at room temperature. After 40 minutes of stirring at the same temperature, to this was added a DMF solution (5 ml) containing 4-chloromethyl-N-(2-methoxyphenyl)benzamide (276 mg, 1.0 mmol) and a catalytically effective amount of sodium iodide. After 2 hours of stirring at 80° C. and subsequent removal of the solvent by evaporation, the resulting residue was mixed with water (10 ml) and extracted with an ethyl acetate-methylene chloride (1:2) mixture solution. The resulting organic layer was washed with water and saturated brine and dried on anhydrous magnesium sulfate. Thereafter, the solvent was removed by evaporation, and the resulting residue was subjected to a silica gel column chromatography (methylene chloride-ether:hexane=2:1) and then washed with ether to obtain 300 mg (77.6%) of the title compound in the form of colorless solid.

Aufarbeitung

  1. customat room temperature
  2. stirringAfter 2 hours of stirring at 80° C.
  3. customsubsequent removal of the solvent
  4. customby evaporation
  5. additionthe resulting residue was mixed with water (10 ml)
  6. extractionextracted with an ethyl acetate-methylene chloride (1:2) mixture solution
  7. washThe resulting organic layer was washed with water and saturated brine
  8. dry with materialdried on anhydrous magnesium sulfate
  9. customThereafter, the solvent was removed by evaporation
  10. washwashed with ether

Quellen und Nachweise

ORD-Eintrag
ord-0629cd8f2ed34187aae991fef93b63da
Quelldatensatz
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US05728835

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