HCID 12748355, Verbindung → 2-(2-Phenyloxazol-5-ylmethyl)isoindole-1,3-dione

HRID 915668Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 915668
Br[CH2:2][C:3]1[O:7][C:6]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)=[N:5][CH:4]=1.[C:14]1(=[O:24])[NH:18][C:17](=[O:19])[C:16]2=[CH:20][CH:21]=[CH:22][CH:23]=[C:15]12.[K]>CN(C)C=O>[C:8]1([C:6]2[O:7][C:3]([CH2:2][N:18]3[C:14](=[O:24])[C:15]4[C:16](=[CH:20][CH:21]=[CH:22][CH:23]=4)[C:17]3=[O:19])=[CH:4][N:5]=2)[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Komponenten

4

Edukt 2

HCID 12748355HCID 12748355, VerbindungHCID 24194345Phthalimide potassium salt

Produkt 1

HCID 691295772-(2-Phenyloxazol-5-ylmethyl)isoindole-1,3-dioneAusbeute 99,8 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

Dissolve 5-bromomethyl-2-phenyloxazole (1.17 g, 4.94 mmol) in dimethylformamide (15 mL) and add dropwise to a solution of potassium phthalimide (1.1 g, 5.93 mmol) in dimethylformamide (15 mL). Stir the reaction under nitrogen at room temperature overnight, concentrate to remove dimethylformamide, dissolve in ethyl acetate (75 mL), wash with saturated Na2CO3 (50 mL), and brine (75 mL). Dry the organic phase (Na2SO4), filter, and concentrate. Perform flash chromatography on silica gel eluting with 4:1 to 1:1 Hex/ethyl acetate to afford 1.5 g of 2-(2-phenyloxazol-5-ylmethyl)isoindole-1,3-dione as an off-white solid. MS: m/e=305 (MH+)

Aufarbeitung

  1. customthe reaction under nitrogen at room temperature overnight
  2. concentrationconcentrate
  3. customto remove dimethylformamide
  4. dissolutiondissolve in ethyl acetate (75 mL)
  5. washwash with saturated Na2CO3 (50 mL), and brine (75 mL)
  6. dry with materialDry the organic phase (Na2SO4)
  7. filtrationfilter
  8. concentrationconcentrate

Quellen und Nachweise

ORD-Eintrag
ord-ead33618bae447eba2633c79213d5575
Quelldatensatz
uspto-grants-2007_09
Patentnummer
US07265246B2

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