Salicylamide → HCID 11682447, Verbindung

HRID 427282Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 427282
[C:1]([NH2:10])(=[O:9])[C:2]1[C:3](=[CH:5][CH:6]=[CH:7][CH:8]=1)[OH:4].C(O[CH:14](OCC)[CH2:15][O:16][C:17]1[CH:22]=[CH:21][C:20]([CH2:23][CH:24]2[S:28][C:27](=[O:29])[NH:26][C:25]2=[O:30])=[CH:19][CH:18]=1)C>C(Cl)(Cl)Cl>[O:9]=[C:1]1[C:2]2[CH:8]=[CH:7][CH:6]=[CH:5][C:3]=2[O:4][CH:14]([CH2:15][O:16][C:17]2[CH:18]=[CH:19][C:20]([CH2:23][CH:24]3[S:28][C:27](=[O:29])[NH:26][C:25]3=[O:30])=[CH:21][CH:22]=2)[NH:10]1

Komponenten

4

Edukt 2

HCID 5147SalicylamideHCID 232983485-[4-(2,2-Diethoxyethoxy)benzyl]thiazolidine-2,4-dione

Produkt 1

HCID 11682447HCID 11682447, VerbindungAusbeute 82 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 6212ChloroformLösungsmittel2×

Versuchsvorschrift

To a stirred solution of polyphosphonate ethyl ester (PPE) (3.15 g, 7.29 mmol) in chloroform (4.0 mL) was added salicylamide (0.5 g, 3.65 mmol) followed by addition of a solution of 5-[4-[(2,2-diethoxy)ethoxy]phenyl methyl]thiazolidin-2,4-dione (1.36 g, 4.0 mmol) obtained in example 2, in chloroform (10 mL) dropwise at 25-30° C. The reaction mixture was immersed in a preheated oil bath and refluxed for 3 h. The reaction mixture was cooled to room temperature and CHCl3 was removed under reduced pressure. To the resultant residue aq. sat. NaHCO3 solution (25 mL) was added and stirred for 30 min. at 25-30° C. The precipitated brown coloured solid was filtered and purified by column chromatography using EtOAc:pet. ether (1:1) to yield the title compound (1.15 g, 81%). mp: 134° C.-138° C.

Aufarbeitung

  1. customThe reaction mixture was immersed in a preheated oil bath
  2. temperaturerefluxed for 3 h
  3. customCHCl3 was removed under reduced pressure
  4. additionTo the resultant residue aq. sat. NaHCO3 solution (25 mL) was added
  5. filtrationThe precipitated brown coloured solid was filtered
  6. custompurified by column chromatography

Quellen und Nachweise

ORD-Eintrag
ord-359284a9cdfb4d7bb1d6c40f12b2d0d0
Quelldatensatz
uspto-grants-2001_11
Patentnummer
US06313113B1

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