Toluene → 6-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione

HRID 860543Notes

Reaction equation

HRID 860543 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:33]=[C:34]5[C:39](=[CH:40][CH:41]=4)[CH:38]=[C:37](C=O)[CH:36]=[CH:35]5)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[S:44]1[CH2:48][C:47](=[O:49])[NH:46][C:45]1=[O:50]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:33]=[C:34]5[C:39](=[CH:40][CH:41]=4)[CH:38]=[C:37]([N:46]4[C:47](=[O:49])[C:48](=[CH2:1])[S:44][C:45]4=[O:50])[CH:36]=[CH:35]5)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[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 865860366-[3-(1-Adamantyl)-4-methoxyphenyl]-2-naphthaldehyde

Product 1

HCID 865860356-[3-(1-Adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedioneYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (150 mL), piperidine (0.48 mL), acetic acid (0.51 mL), 6-[3-(1-adamantyl)-4-methoxyphenyl]-2-naphthaldehyde (5.84 g, 14.75 mmol) and 2,4-thiazolidinedione (1.73 g, 14.75 mmol) was heated at reflux for 18 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in 30 mL of EtOH. After 30 minutes the solid was filtered and dried under high vacuum to afford 5.3 g (71%) of 6-[3-(1-adamantyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 286–287° C. 1H NMR (300 MHz; DMSO-d6): 1.76 (brs, 6H), 2.07–2.14 (m, 9H), 3.87 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.58 (s, 1H), 7.66 (t, J=9.3 Hz, 2H), 7.88–7.93 (m, 2H), 8.09 (t, J=8.7 Hz, 2H), 8.18 (d, J=5.7 Hz, 2H), 12.63 (brs, 1H).

Workup

  1. temperatureat reflux for 18 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. filtrationAfter 30 minutes the solid was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-eb188f8f51524e299b203239e75c454e
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

Loading…