Toluene → 6-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone

HRID 860561Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 860561
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31](C=O)[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:16])[CH3:15].[S:38]=[C:39]1[NH:43][C:42](=[O:44])[CH2:41][S:40]1>C(O)(=O)C>[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([N:43]2[C:42](=[O:44])[C:41](=[CH2:1])[S:40][C:39]2=[S:38])[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:15])[CH3:16]

Komponenten

6

Edukt 4

HCID 1140TolueneHCID 8082PiperidineHCID 1201546RhodanineHCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

Produkt 1

HCID 865860446-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinoneAusbeute 56 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 176Acetic AcidLösungsmittel

Versuchsvorschrift

A solution of toluene (2.5 mL), piperidine (0.003 mL), acetic acid (0.003 mL), 6-[3-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (0.100 g, 0.31 mmol) and 2-thioxo-4-thiazolidinone (0.041 mg, 0.31 mmol) was heated at reflux for 16.5 hours under an argon atmosphere. The resulting suspension was filtered and the solid was washed with EtOH and H2O. The solid was dried under high vacuum to afford 0.076 g (56%) of 6-[3-(t-butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone, mp 281–284° C. 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.86 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.61–7.70 (m, 3H), 7.77 (s, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.09 (dd, J1=8.4 Hz, J2=3.0 Hz, 2H), 8.10 (s, 2H), 13.9 (brs, 1H).

Aufarbeitung

  1. temperatureat reflux for 16.5 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with EtOH and H2O
  4. customThe solid was dried under high vacuum

Quellen und Nachweise

ORD-Eintrag
ord-ff2e6de02c814dfe901a58c9ba7b41af
Quelldatensatz
uspto-grants-2006_12
Patentnummer
US07153875B2

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