Sodium Hydroxide → HCID 67273043, Verbindung

HRID 1698544Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1698544
[CH2:1]([C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[C:14]2[N:15]([CH3:19])[C:16](=O)[NH:17][C:13]=2[CH:12]=[CH:11][CH:10]=1)[CH3:2].P(Cl)(Cl)([Cl:22])=O.[OH-].[Na+]>>[Cl:22][C:16]1[N:15]([CH3:19])[C:14]2[C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[CH2:1][CH3:2])=[CH:10][CH:11]=[CH:12][C:13]=2[N:17]=1

Komponenten

4

Edukt 3

HCID 14798Sodium HydroxideHCID 24813Phosphorus oxychlorideHCID 67272898HCID 67272898, Verbindung

Produkt 1

HCID 67273043HCID 67273043, VerbindungAusbeute 60 %

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

A mixture of 190 mg (0.753 mmol) of 7-(2-ethylphenyl)-1-methyl-1,3-dihydro-2H-benzimidazol-2-one and 1.5 mL of phosphorus oxychloride was stirred at 80° C. for 5 hours. After cooling, the reaction mixture was poured into ice and neutralized by 12 N sodium hydroxide. The aqueous suspension was extracted with ethyl acetate (X2). The combined organic layer was washed with brine (X1), dried over sodium sulfate and concentrated in vacuo. The residue was purified by silica gel column chromatography eluting with a 3-10% ethylacetate/n-hexane gradient mixture to give 123 mg (60%) of the title compound.

Aufarbeitung

  1. temperatureAfter cooling
  2. additionthe reaction mixture was poured into ice
  3. extractionThe aqueous suspension was extracted with ethyl acetate (X2)
  4. washThe combined organic layer was washed with brine (X1)
  5. dry with materialdried over sodium sulfate
  6. concentrationconcentrated in vacuo
  7. customThe residue was purified by silica gel column chromatography
  8. washeluting with a 3-10% ethylacetate/n-hexane gradient mixture

Quellen und Nachweise

ORD-Eintrag
ord-fae8eb71bb244c148d725b37a9193017
Quelldatensatz
uspto-grants-2012_04
Patentnummer
US08163935B2

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