Triphenylphosphine → (Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

HRID 517570Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517570
[CH2:1]([O:3][C:4]1[CH:17]=[CH:16][C:7](/[CH:8]=[C:9]2/[C:10](=[O:15])[NH:11][C:12](=[O:14])[S:13]/2)=[CH:6][CH:5]=1)[CH3:2].[C:18]([NH:37]CCO)(C1C=CC=CC=1)(C1C=CC=CC=1)[C:19]1C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1.C(OCC)(=O)C>[NH2:37][CH2:18][CH2:19][N:11]1[C:10](=[O:15])/[C:9](=[CH:8]/[C:7]2[CH:16]=[CH:17][C:4]([O:3][CH2:1][CH3:2])=[CH:5][CH:6]=2)/[S:13][C:12]1=[O:14]

Komponenten

7

Edukt 4

HCID 11776TriphenylphosphineHCID 31256082-((Triphenylmethyl)amino)ethanolHCID 5363146Diisopropyl azodicarboxylateHCID 5878179(Z)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dione

Produkt 1

HCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneAusbeute 182,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 8028TetrahydrofuranLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Compound 2 (1.26 g, 5.08 mmol), 2-(tritylamino)ethanol (2.00 g, 6.60 mmol) and triphenylphosphine (1.80 g, 6.86 mmol) were dissolved in 51 mL of anhydrous THF, and stirred at room temperature for 5 min. DIAD (1.3 mL, 6.60 mmol) was added to the reaction mixture and then stirred overnight at 45° C. The reaction mixture was diluted with ethyl acetate and washed with sat'd NH4Cl aqueous solution. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (30% ethyl acetate in hexanes) to afford 3 (75.0%, 2.71 g) as a white solid.

Aufarbeitung

  1. stirringstirred overnight at 45° C
  2. washwashed with sat'd NH4Cl aqueous solution
  3. customThe organic layer was collected
  4. dry with materialdried over anhydrous Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated
  7. custompurified by silica column chromatography (30% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-857af05a6f5048b286be6d7c0070d824
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115122B2

Notizen zur Reaktion

Wird geladen…