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

HRID 860564Notes

Reaction equation

HRID 860564 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[CH3:14][C:15]1([C:21]2[CH:22]=[C:23]([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:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:20][CH2:19][CH2:18][CH2:17][CH2:16]1.[S:41]1[CH2:45][C:44](=[O:46])[NH:43][C:42]1=[O:47]>C(O)(=O)C>[CH3:14][C:15]1([C:21]2[CH:22]=[C:23]([C:29]3[CH:30]=[C:31]4[C:36](=[CH:37][CH:38]=3)[CH:35]=[C:34]([N:43]3[C:44](=[O:46])[C:45](=[CH2:1])[S:41][C:42]3=[O:47])[CH:33]=[CH:32]4)[CH:24]=[CH:25][C:26]=2[O:27][CH3:28])[CH2:16][CH2:17][CH2:18][CH2:19][CH2:20]1

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860476-[3-(1-Methylcyclohexyl)-4-methoxyphenyl]-2-naphthaldehyde

Product 1

HCID 865860466-[3-(1-Methylcyclohexyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedioneYield 37%

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-(1-methylcyclohexyl)-4-methoxyphenyl]-2-naphthaldehyde (0.100 g, 0.28 mmol) and 2,4-thiazolidinedione (0.033 mg, 0.28 mmol) was heated at reflux for 15 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 0.048 g (37%) of 6-[3-(1-methylcyclohexyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2,4-thiazolidinedione, mp 268–271° C. 1H NMR (300 MHz, DMSO-d6): δ 1.21–1.61 (m, 9H), 1.69–1.81 (m, 2H), 2.15 (t, J=10.7 Hz, 2H), 3.86 (s, 3H), 7.14 (d, J=8.7 Hz, 1H), 7.65 (s, 1H), 7.69 (brt, J=9.6 Hz, 2H), 7.90 (d, J=9.9 Hz, 1H), 7.94 (s, 1H), 8.10 (d, J=8.7 Hz, 1H), 8.12 (d, J=8.7 Hz, 1H), 8.19 (s, 2H), 12.66 (brs, 1H).

Workup

  1. temperatureat reflux for 15 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-29c76f19915f44649e7f15963b7bb3a2
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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