Toluene → HCID 86586039, compound

HRID 860550Notes

Reaction equation

HRID 860550 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]1([C:20]2[CH:21]=[C:22]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[CH:34]=[C:33](C=O)[CH:32]=[CH:31]4)[CH:23]=[CH:24][C:25]=2[O:26][CH3:27])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[S:40]1[CH2:44][C:43](=[O:45])[NH:42][C:41]1=[O:46]>C(O)(=O)C>[C:14]1([C:20]2[CH:21]=[C:22]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[CH:34]=[C:33]([N:42]3[C:43](=[O:45])[C:44](=[CH2:1])[S:40][C:41]3=[O:46])[CH:32]=[CH:31]4)[CH:23]=[CH:24][C:25]=2[O:26][CH3:27])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860406-(3-Phenyl-4-methoxyphenyl)-2-naphthaldehyde

Product 1

HCID 86586039HCID 86586039, compoundYield 14%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of toluene (2.5 mL), piperidine (0.003 mL), acetic acid (0.004 mL), 6-[3-phenyl-4-methoxyphenyl]-2-naphthaldehyde (0.124 g, 0.37 mmol) and 2,4-thiazolidinedione (0.043 mg, 0.37 mmol) was heated at reflux for 20 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 0.023 g (14%) of 6-(3-phenyl-4-methoxyphenyl)-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 221–224° C. 1H NMR (300 MHz, DMSO-d6): δ 3.85 (s, 3H), 7.28 (d, J=8.4 Hz, 1H), 7.38 (d, J=8.1 Hz, 1H), 7.46 (t, J=7.0 Hz, 2H), 7.60 (d, J=8.4 Hz, 2H), 7.70 (d, J=8.4 Hz, 1H), 7.77 (s, 1H), 7.86 (d, J=8.4 Hz, 1H), 7.94 (s, 1H), 8.00 (d, J=8.4 Hz, 1H), 8.10 (d, J=8.4 Hz, 2H), 8.20 (s, 1H), 8.32 (s, 1H), 12.66 (brs, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 hours under an argon atmosphere
  3. filtrationThe resulting suspension was filtered
  4. filtrationthe solid was filtered
  5. customdried under high vacuum

Sources & evidence

ORD record
ord-2409dbb1bd724ce09c101eaa3ee28e98
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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