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

HRID 860556Notes

Reaction equation

HRID 860556 reaction equation
[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]1[CH2:42][C:41](=[O:43])[NH:40][C:39]1=[O:44]>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:40]2[C:41](=[O:43])[C:42](=[CH2:1])[S:38][C:39]2=[O:44])[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:15])([CH3:17])[CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

Product 1

HCID 865860426-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedioneYield 28%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (2.5 mL), piperidine (0.003 mL), acetic acid (0.003 mL), 6-[3-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (0.124 g, 0.31 mmol) and 2,4-thiazolidinedione (0.036 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 stirred at room temperature in EtOH. After 3 hours, the solid was filtered and dried under high vacuum to afford 0.037 g (28%) of 6-[3-(t-butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 274–276° C. 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.86 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.63 (s, 1H), 7.66 (t, J=8.1 Hz, 2H), 7.88 (d, J=8.4 Hz, 1H), 7.92 (s, 1H), 8.07 (d, J=8.4 Hz, 1H), 8.08 (d, J=8.4 Hz, 1H), 8.17 (brs, 2H), 12.60 (brs, 1H).

Workup

  1. temperatureat reflux for 16.5 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. filtrationthe solid was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-245b17a7f23f4ecc8a67d40c045f6145
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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