Thiazolidinedione → 5-[3-(1-Methyl-cyclohexylmethoxy)-benzylidene]-thiazolidine-2,4-dione

HRID 1009185Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1009185
[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=O)[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1.[S:18]1[CH2:22][C:21](=[O:23])[NH:20][C:19]1=[O:24].N1CCCCC1>CCO>[CH3:1][C:2]1([CH2:8][O:9][C:10]2[CH:11]=[C:12]([CH:15]=[CH:16][CH:17]=2)[CH:13]=[C:22]2[S:18][C:19](=[O:24])[NH:20][C:21]2=[O:23])[CH2:7][CH2:6][CH2:5][CH2:4][CH2:3]1

Komponenten

5

Edukt 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 248277673-(1-Methyl-cyclohexylmethoxy)-benzaldehyde

Produkt 1

HCID 743268405-[3-(1-Methyl-cyclohexylmethoxy)-benzylidene]-thiazolidine-2,4-dioneAusbeute 67 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 702EthanolLösungsmittel

Versuchsvorschrift

A mixture consisting of compound v (0.5 mmol), 2,4-thiazolidinedione (0.6 mmol) and catalytic amounts of piperidine was refluxed in EtOH (5 mL) for 24 h and then concentrated. The oily product was dissolved in ethyl acetate, poured into water and acidified with AcOH. The solution was extracted with ethyl acetate, dried and concentrated. The residue was purified by silica gel chromatography, providing compound 1 in 67% yield. 1H NMR (300 MHz, CDCl3) δ 1.04 (s, 3H), 1.46-1.56 (m, 10H), 3.69 (s, 2H), 6.78-7.28 (m, 2H), 7.08 (d, J=8.40 Hz, 1H), 7.39 (dt, J=2.10, 8.40 Hz, 1H), 7.84 (s, 1H), 8.21-8.78 (br, 1H); HRMS exact mass of (M+Na)+, 354.1140 amu; observed mass of (M+Na)+, 354.113 amu.

Aufarbeitung

  1. concentrationconcentrated
  2. dissolutionThe oily product was dissolved in ethyl acetate
  3. additionpoured into water
  4. extractionThe solution was extracted with ethyl acetate
  5. customdried
  6. concentrationconcentrated
  7. customThe residue was purified by silica gel chromatography

Quellen und Nachweise

ORD-Eintrag
ord-34d2f38f0d8d4bcb9802ac92f3150759
Quelldatensatz
uspto-grants-2011_07
Patentnummer
US07973062B2

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