Toluene → HCID 86586028, compound

HRID 860527Notes

Reaction equation

HRID 860527 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:33]4[CH:34]=[C:35]5[C:40](=[CH:41][CH:42]=4)[CH:39]=[C:38](C=O)[CH:37]=[CH:36]5)[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:45]1[CH2:49][C:48](=[O:50])[NH:47][C:46]1=[O:51]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:33]4[CH:34]=[C:35]5[C:40](=[CH:41][CH:42]=4)[CH:39]=[C:38]([N:47]4[C:48](=[O:50])[C:49](=[CH2:1])[S:45][C:46]4=[O:51])[CH:37]=[CH:36]5)[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

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86586029HCID 86586029, compound

Product 1

HCID 86586028HCID 86586028, compoundYield 69%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A mixture of toluene (10 mL), piperidine (10 μL), acetic acid (10 μL), 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-2-naphthaldehyde (0.400 g, 0.974 mmol) and 2,4-thiazolidinedione (0.114 g, 0.974 mmol) was heated at reflux overnight under an argon atmosphere. The reaction mixture was cooled to room temperature, and the resulting crystalline compound was filtered, washed with toluene and ethanol. The yellow solid was dried under high vacuum to afford 0.344 g (69%) of 6-[3-(1-adamantyl)-4,5-methylenedioxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 304–306° (dec). 1H NMR (500 MHz; DMSO-d6): 1.76 (s, 6H), 2.07 (s, 9H), 6.06 (s, 2H), 7.16 (d, J=1.6 Hz, 1H), 7.29 (s, 1H), 7.68 (dd, J=1.0 Hz, J=9.0 Hz, 1H), 7.88 (d, J=9.0 Hz, 1H), 7.93 (s, 1H), 8.06 (d, J=9.0 Hz, 1H), 8.08 (d, J=8.8 Hz, 1H), 8.17 (s, 1H), 8.19 (s, 1H), 12.5–12.7 (brs, 1H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux overnight under an argon atmosphere
  3. filtrationthe resulting crystalline compound was filtered
  4. washwashed with toluene and ethanol
  5. customThe yellow solid was dried under high vacuum

Sources & evidence

ORD record
ord-a2ed4a4589fe4959a019951fc44a8eb3
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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