Hydrochloric Acid → 3-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-one

HRID 1263712

Reaktionsgleichung

Reaktionsgleichung von HRID 1263712
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[CH:7][CH:8]=2)[CH2:3][C:2]1=[O:10].C[Si](C)(C)N[Si](C)(C)C.[Na].[NH2:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][O:27][C:28]2=O)=[CH:24][CH:23]=1.Cl>CN(C=O)C>[NH2:21][C:22]1[CH:31]=[C:30]2[C:25]([CH2:26][O:27][C:28]2=[C:3]2[C:4]3[C:9](=[CH:8][CH:7]=[CH:6][CH:5]=3)[NH:1][C:2]2=[O:10])=[CH:24][CH:23]=1

Komponenten

6

Edukt 4

HCID 313Hydrochloric AcidHCID 936316-AminophthalideHCID 321710OxindoleHCID 45051731Sodium hexamethyidisilazane

Produkt 1

HCID 696591993-(6-Amino-2-benzofuran-1(3H)-ylidene)-1,3-dihydro-2H-indol-2-oneAusbeute 45 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6228DimethylformamideLösungsmittel2×

Versuchsvorschrift

To a solution containing oxindole (0.5 g, 3.76 mmol) in 7.5 mL DMF was added 7.51 mL of sodium hexamethyldisilazane (1.0 M in THF) over 3 min. After stirring 10 min at room temperature, a solution of 6-aminophthalide (0.672 g, 4.51 mmol) in 4.0 mL DMF was added over 3 min. The reaction was stirred for 50 min at room temperature and then poured into 4% HCl to give a yellow solid. The solid was filtered to a wet cake and then partitioned between EtOAc and saturated NaHCO3. Then the mixture was heated to dissolve the solid. The organic phase was washed with H2O, brine and then dried with Na2SO4. The solvent was removed in vacuo and the resultant solid triturated with CHCl3 to afford the title compound (445 mg, 45%) as a yellow solid.

Aufarbeitung

  1. stirringThe reaction was stirred for 50 min at room temperature
  2. customto give a yellow solid
  3. filtrationThe solid was filtered to a wet cake
  4. custompartitioned between EtOAc and saturated NaHCO3
  5. temperatureThen the mixture was heated
  6. dissolutionto dissolve the solid
  7. washThe organic phase was washed with H2O, brine
  8. dry with materialdried with Na2SO4
  9. customThe solvent was removed in vacuo
  10. customthe resultant solid triturated with CHCl3

Quellen und Nachweise

ORD-Eintrag
ord-c2a7fa1e3a864aa098abed3b9d4d5688
Quelldatensatz
uspto-grants-2003_04
Patentnummer
US06541504B1

Verknüpfte Notizen

Wird geladen…