Toluene → 6-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone

HRID 860561Notes

Reaction equation

HRID 860561 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31](C=O)[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:16])[CH3:15].[S:38]=[C:39]1[NH:43][C:42](=[O:44])[CH2:41][S:40]1>C(O)(=O)C>[C:14]([C:18]1[CH:19]=[C:20]([C:26]2[CH:27]=[C:28]3[C:33](=[CH:34][CH:35]=2)[CH:32]=[C:31]([N:43]2[C:42](=[O:44])[C:41](=[CH2:1])[S:40][C:39]2=[S:38])[CH:30]=[CH:29]3)[CH:21]=[CH:22][C:23]=1[O:24][CH3:25])([CH3:17])([CH3:15])[CH3:16]

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 1201546RhodanineHCID 865860436-[3-(t-Butyl)-4-methoxyphenyl]-2-naphthaldehyde

Product 1

HCID 865860446-[3-(t-Butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinoneYield 56%

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-(t-butyl)-4-methoxyphenyl]-2-naphthaldehyde (0.100 g, 0.31 mmol) and 2-thioxo-4-thiazolidinone (0.041 mg, 0.31 mmol) was heated at reflux for 16.5 hours under an argon atmosphere. The resulting suspension was filtered and the solid was washed with EtOH and H2O. The solid was dried under high vacuum to afford 0.076 g (56%) of 6-[3-(t-butyl)-4-methoxyphenyl]-naphthalen-2-yl-methylene-2-thioxo-4-thiazolidinone, mp 281–284° C. 1H NMR (300 MHz, DMSO-d6): δ 1.40 (s, 9H), 3.86 (s, 3H), 7.11 (d, J=8.4 Hz, 1H), 7.61–7.70 (m, 3H), 7.77 (s, 1H), 7.89 (d, J=8.4 Hz, 1H), 8.09 (dd, J1=8.4 Hz, J2=3.0 Hz, 2H), 8.10 (s, 2H), 13.9 (brs, 1H).

Workup

  1. temperatureat reflux for 16.5 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered
  3. washthe solid was washed with EtOH and H2O
  4. customThe solid was dried under high vacuum

Sources & evidence

ORD record
ord-ff2e6de02c814dfe901a58c9ba7b41af
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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