Toluene → HCID 86586049, compound

HRID 860572Notes

Reaction equation

HRID 860572 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][CH:38]=3)[CH:35]=[C:34](C=O)[CH:33]=[CH:32]4)[CH:23]=[C:24]3[O:28][CH2:27][O:26][C:25]=23)[CH:15]=1.[S:41]1[CH2:45][C:44](=[O:46])[NH:43][C:42]1=[O:47]>C(O)(=O)C>[N:14]1[CH:19]=[CH:18][CH:17]=[C:16]([C:20]2[CH:21]=[C:22]([C:29]3[CH:30]=[C:31]4[C:32](=[CH:37][CH:38]=3)[CH:33]=[C:34]([N:43]3[C:44](=[O:46])[C:45](=[CH2:1])[S:41][C:42]3=[O:47])[CH:35]=[CH:36]4)[CH:23]=[C:24]3[O:28][CH2:27][O:26][C:25]=23)[CH:15]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86586050HCID 86586050, compound

Product 1

HCID 86586049HCID 86586049, compound

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (8 mL), piperidine (0.008 mL), acetic acid (0.009 mL) and 6-[3-(3-pyridyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde (0.304 g, 0.86 mmol) and 2,4-thiazolidinedione (101 mg, 0.86 mmol) was heated at reflux for 16 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in EtOH. After 1 hours, the solid was filtered and dried under high vacuum to afford 78.0 mg of 6-[3-(3-pyridyl)-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 298–300° C. 1H NMR (300 MHz, DMSO-d6): δ 6.16 (s, 2H), 7.10–7.28 (m, 4H), 7.51 (dt, J1=8.0 Hz, J2=1.5 Hz, 1H), 7.66 (dd, J1=8.4 Hz, J2=1.8 Hz, 1H), 7.75–7.85 (m, 2H), 7.90 (s, 1H), 7.93 (d, J=8.7 Hz, 1H), 8.11 (s, 1H), 8.25 (d, J=1.5 Hz, 1H), 8.34 (dd, J1=4.8 Hz, J2=1.4 Hz, 1H), 12.69 (brs, 1H).

Workup

  1. temperatureat reflux for 16 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-6c1c43078c494d1c886515a2445aad6b
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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