Piperonal → HCID 178457008, Verbindung

HRID 1865327

Reaktionsgleichung

Reaktionsgleichung von HRID 1865327
[C:1]1([N:7]2[C:11](=[O:12])[CH2:10][S:9]/[C:8]/2=[N:13]\[CH:14]([CH3:16])[CH3:15])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[CH:17]1[C:22]([CH:23]=O)=[CH:21][C:20]2[O:25][CH2:26][O:27][C:19]=2[CH:18]=1.C([O-])(=O)C.[Na+]>C(O)(=O)C.CC(=O)OCC>[O:27]1[C:19]2[CH:18]=[CH:17][C:22](/[CH:23]=[C:10]3/[C:11](=[O:12])[N:7]([C:1]4[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=4)/[C:8](=[N:13]/[CH:14]([CH3:16])[CH3:15])/[S:9]/3)=[CH:21][C:20]=2[O:25][CH2:26]1

Komponenten

6

Edukt 3

HCID 8438PiperonalHCID 517045Sodium AcetateHCID 178457009HCID 178457009, Verbindung

Produkt 1

HCID 178457008HCID 178457008, Verbindung

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 176Acetic AcidLösungsmittelHCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

A solution of 3-phenyl-2-[(Z)-isopropylimino]-thiazolidin-4-one (150 mg, 0.64 mmol), piperonal (192 mg, 1.28 mmol) and sodium acetate (105 mg, 1.28 mmol) in acetic acid (3 mL) is stirred at 110° C. for 4 h. The dark yellow to brown solution is cooled to rt, diluted with EA (75 mL), washed with sat. aq. NaHCO3, followed by water, and evaporated. The crude product is purified by crystallisation from a small amount of methanol (approx. 5 mL) to give 5-benzo[1,3]dioxol-5-ylmeth-(Z)-ylidene-2-[(Z)-isopropylimino]-3-phenyl-thiazolidin-4-one.

Aufarbeitung

  1. washwashed with sat. aq. NaHCO3
  2. customevaporated
  3. customThe crude product is purified by crystallisation from a small amount of methanol (approx. 5 mL)

Quellen und Nachweise

ORD-Eintrag
ord-052c9b1cfa7045abaacd854faf4a3ef2
Quelldatensatz
uspto-grants-2009_12
Patentnummer
US07626037B2

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