Ethanol → [4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-urea

HRID 1023438Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1023438
[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH2:15])[CH:10]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[C:23]([N:31]=C=O)(=[O:30])C1C=CC=CC=1.C(O)C.C(=O)([O-])[O-].[K+].[K+]>C(Cl)Cl>[C:1]1([C:7]([C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=2[CH3:22])=[CH:8][C:9]2[CH:14]=[CH:13][N:12]=[C:11]([NH:15][C:23]([NH2:31])=[O:30])[CH:10]=2)[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=1

Komponenten

6

Edukt 4

HCID 702EthanolHCID 11430Potassium CarbonateHCID 78210Benzoyl isocyanateHCID 690856204-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-ylamine

Produkt 1

HCID 69083977[4-(2-Phenyl-2-o-tolyl-vinyl)-pyridin-2-yl]-ureaAusbeute 64,1 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6344DichloromethaneLösungsmittel

Reaktionsbedingungen

Temperatur
50 °C

Versuchsvorschrift

The crude 4-(2-phenyl-2-o-tolyl-vinyl)-pyridin-2-ylamine (251 mg) is dissolved in methylene chloride (5 mL). Then benzoyl isocynate (258 mg, 1.75 mmol) is added. The reaction mixture is sealed and heated at 50° C. for 16 hour. The solvent is then carefully removed and to the residue are added ethanol (5 mL) and potassium carbonate (182 mg, 1.32 mmol). The resulting mixture is heated at 80° C. for 45 min. Then solvent is removed and the residue is partitioned between water (45 mL) and EtOAc (55 mL). The aqueous layer is separated and extracted with EtOAc (2×30 mL). The organic layers are combined and concentrated to give the crude product. Purification by silica flash column chromatography using MeOH in DCM (gradient from 0% to 10%) affords 185 mg of the desired product.

Aufarbeitung

  1. customThe reaction mixture is sealed
  2. customThe solvent is then carefully removed and to the residue
  3. temperatureThe resulting mixture is heated at 80° C. for 45 min
  4. customThen solvent is removed
  5. customthe residue is partitioned between water (45 mL) and EtOAc (55 mL)
  6. customThe aqueous layer is separated
  7. extractionextracted with EtOAc (2×30 mL)
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by silica flash column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-ff7a81728e26460da7138b3dd27900a8
Quelldatensatz
uspto-grants-2014_05
Patentnummer
US08722709B2

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