Acetic Acid → 4-[3-(1-Adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione
Reaktionsgleichung
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=[C:42]1[NH:46][C:45](=[O:47])[CH2:44][S:43]1.C(O)(=[O:50])C>>[C:14]12([C:24]3[CH:25]=[C:26]([C:33]4[CH:34]=[CH:35][C:36]([CH:37]=[C:44]5[S:43][C:42](=[O:50])[NH:46][C:45]5=[O:47])=[CH:39][CH:40]=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]2Komponenten
Versuchsvorschrift
A solution of toluene (100 mL), piperidine (100 μL), acetic acid (100 μL), 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzaldehyde (1.50 g, 4.16 mmol, see Example 1a) and 2-thioxo-4-thiazolidinone (0.554 g, 4.16 mmol) was heated at reflux overnight under an argon atmosphere. Within 20 minutes an orange-yellow solid formed. A Dean-Stark trap was attached and after 48 hours the reaction mixture was cooled to room temperature, and the resulting crystalline compound was filtered and washed with ethanol. The yellow solid was dried under high vacuum to afford 1.50 g (76%) of 4-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione, mp 337.5–338.5° (dec). 1H NMR (500 MHz; DMSO-d6): 1.75 (s, 6H), 2.05 (s, 9H), 6.05 (s, 2H), 7.07 (s, 1H), 7.22 (s, 1H), 7.63 (d, J=8.0 Hz, 1H), 7.80 (d, J=8.0 Hz, 1H), 13.6–13.9 (brs, 1H).
Aufarbeitung
- temperatureat reflux overnight under an argon atmosphere
- customWithin 20 minutes an orange-yellow solid formed
- filtrationthe resulting crystalline compound was filtered
- washwashed with ethanol
- customThe yellow solid was dried under high vacuum
Quellen und Nachweise
- ORD-Eintrag
- ord-7b328c25511548b88161e7cc7d77550f
- Quelldatensatz
- uspto-grants-2006_12
- Patentnummer
- US07153875B2
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