Toluene → 4-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione

HRID 860523Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860523
C1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:33]4[CH:40]=[CH:39][C:36]([CH:37]=O)=[CH:35][CH:34]=4)[CH:27]=[C:28]4[O:32][CH2:31][O:30][C:29]=34)[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[S:41]1[CH2:45][C:44](=[O:46])[NH:43][C:42]1=[O:47]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:33]4[CH:40]=[CH:39][C:36]([CH:37]=[C:45]5[S:41][C:42](=[O:47])[NH:43][C:44]5=[O:46])=[CH:35][CH:34]=4)[CH:27]=[C:28]4[O:32][CH2:31][O:30][C:29]=34)[CH2:23][CH:18]3[CH2:17][CH:16]([CH2:22][CH:20]([CH2:19]3)[CH2:21]1)[CH2:15]2

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 101554434-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde

Produkt 1

HCID 724165534-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedioneAusbeute 76,5 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of toluene (10 mL), piperidine (10 μL), acetic acid (10 μL), 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde (0.400 g, 1.11 mmol) and 2,4-thiazolidinedione (0.130 g, 1.11 mmol) was heated at reflux overnight under an argon atmosphere. The reaction mixture was cooled to room temperature, and the resulting crystalline compound was filtered, washed with toluene and ethanol. The yellow solid was dried under high vacuum to afford 0.390 g (76%) of 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione, mp 308° (dec). 1H NMR (500 MHz; DMSO-d6): 1.74 (s, 6H), 2.04 (s, 9H), 6.05 (s, 2H), 7.06 (d, J=1.5 Hz, 1H), 7.20 (d, J=1.5 Hz, 1H), 7.63 (d, J=8.0 Hz, 2H), 7.78 (d, J=8.0 Hz, 2H), 7.81 (s, 1H), 12.5–12.7 (brs, 1H).

Aufarbeitung

  1. temperatureat reflux overnight under an argon atmosphere
  2. filtrationthe resulting crystalline compound was filtered
  3. washwashed with toluene and ethanol
  4. customThe yellow solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-03d80f3777614300a7ea32710f1653ea
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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