Hydrochloric Acid → 5-(4-Ethoxybenzyl)thiazolidine-2,4-dione

HRID 517571Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 517571
[BH4-].[Li+].NCC[N:6]1[C:10](=[O:11])/[C:9](=[CH:12]/[C:13]2[CH:18]=[CH:17][C:16]([O:19][CH2:20][CH3:21])=[CH:15][CH:14]=2)/[S:8][C:7]1=[O:22].Cl>C1COCC1.N1C=CC=CC=1>[CH2:20]([O:19][C:16]1[CH:17]=[CH:18][C:13]([CH2:12][CH:9]2[S:8][C:7](=[O:22])[NH:6][C:10]2=[O:11])=[CH:14][CH:15]=1)[CH3:21]

Komponenten

5

Edukt 3

HCID 313Hydrochloric AcidHCID 1249836(Z)-3-(2-aminoethyl)-5-(4-ethoxybenzylidene)thiazolidine-2,4-dioneHCID 4148881Lithium borohydride

Produkt 1

HCID 443197195-(4-Ethoxybenzyl)thiazolidine-2,4-dione

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 16069498Pyridine tetrahydrofuranLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

To a suspension of lithium borohydride (0.22 g, 10.04 mmol) in 40 mL of THF-pyridine (ratio 1:1), compound 3 (1.00 g, 4.02 mmol) was added at 0° C. The reaction mixture was stirred at 80° C. for 12 h and then cooled to 0° C. 21 mL of 4 N HCl aqueous solution was added carefully and the resulting suspension was stirred at 0° C. for 10 min, and refluxed for 1 h. After cooling down at room temperature, the solvent was removed by evaporation. The residue was dissolved in ethyl acetate and washed with water. The organic layer was collected, dried over anhydrous Na2SO4, filtered, concentrated and purified by silica column chromatography (50% ethyl acetate in hexanes) to afford compound 4 in 76.6% (0.77 g) yield as a colorless oil.

Aufarbeitung

  1. additionwas added at 0° C
  2. temperaturecooled to 0° C
  3. stirringthe resulting suspension was stirred at 0° C. for 10 min
  4. temperaturerefluxed for 1 h
  5. temperatureAfter cooling down at room temperature
  6. customthe solvent was removed by evaporation
  7. dissolutionThe residue was dissolved in ethyl acetate
  8. washwashed with water
  9. customThe organic layer was collected
  10. dry with materialdried over anhydrous Na2SO4
  11. filtrationfiltered
  12. concentrationconcentrated
  13. custompurified by silica column chromatography (50% ethyl acetate in hexanes)

Quellen und Nachweise

ORD-Eintrag
ord-92dff426956c42968ac2d0cb4611130c
Quelldatensatz
uspto-grants-2015_08
Patentnummer
US09115122B2

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