Citric Acid → 4-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehyde

HRID 2217633

Reaktionsgleichung

Reaktionsgleichung von HRID 2217633
[OH:1][C:2]1[CH:15]=[CH:14][C:5]([CH2:6][CH:7]2[S:11][C:10](=[O:12])[NH:9][C:8]2=[O:13])=[CH:4][CH:3]=1.F[C:17]1[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=1.C([O-])([O-])=O.[Cs+].[Cs+].C(O)(=O)CC(CC(O)=O)(C(O)=O)O>CN(C=O)C.C(OCC)(=O)C>[O:12]=[C:10]1[NH:9][C:8](=[O:13])[CH:7]([CH2:6][C:5]2[CH:14]=[CH:15][C:2]([O:1][C:17]3[CH:24]=[CH:23][C:20]([CH:21]=[O:22])=[CH:19][CH:18]=3)=[CH:3][CH:4]=2)[S:11]1

Komponenten

7

Edukt 4

HCID 311Citric AcidHCID 10796Cesium carbonateHCID 680234-FluorobenzaldehydeHCID 101983975-(4-Hydroxybenzyl)thiazolidine-2,4-dione

Produkt 1

HCID 597682934-[4-(2,4-Dioxothiazolidin-5-ylmethyl)-phenoxy]-benzaldehydeAusbeute 65,6 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 6228DimethylformamideLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

To a solution of 52 (5.35 g, 24 mmol) in DMF (150 mL) was added 4-fluorobenzaldehyde (3.00 g, 24 mmol) and Cs2CO3 (20 g, 62 mmol) and the mixture was heated to 100° C. for 2 h. The mixture was poured over vigorously stirring 10% citric acid (200 mL) and ethyl acetate (200 mL). The organic layer was washed with water (300 mL), brine (300 mL), dried (MgSO4), filtered and concentrated in vacuo. The crude product was triturated in hexanes-ethyl acetate (2:1) to yield a white solid (5.15 g, 65%). 1H NMR: (400 MHz, DMSO-d6): δ 12.07 (bs, 1H), 9.92 (s, 1H), 7.92 (d, J=8.8 Hz, 2H), 7.35 (d, J=8.4 Hz, 2H), 7.12 (d, J=8.4 Hz, 2H), 7.09 (d, J=8.4 Hz, 2H) 4.94 (dd, J=8.4 and 4.4 Hz, 1H), 3.41 (dd, J=14.4 and 4.4 Hz, 1H), 3.17 (dd, J=14.4 and 9.2 Hz, 1H).

Aufarbeitung

  1. additionThe mixture was poured
  2. washThe organic layer was washed with water (300 mL), brine (300 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was triturated in hexanes-ethyl acetate (2:1)

Quellen und Nachweise

ORD-Eintrag
ord-72d878deb2b84d0185f350b9df887b87
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07407978B2

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