Toluene → HCID 86586041, compound

HRID 860555Notes

Reaction equation

HRID 860555 reaction equation
[C:1]1(C)C=CC=CC=1.N1CCCCC1.[C:14]1([C:20]2[CH:21]=[C:22]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[CH:34]=[C:33](C=O)[CH:32]=[CH:31]4)[CH:23]=[CH:24][C:25]=2[O:26][CH3:27])[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1.[S:40]=[C:41]1[NH:45][C:44](=[O:46])[CH2:43][S:42]1>C(O)(=O)C>[C:14]1([C:20]2[CH:21]=[C:22]([C:28]3[CH:29]=[C:30]4[C:35](=[CH:36][CH:37]=3)[CH:34]=[C:33]([N:45]3[C:44](=[O:46])[C:43](=[CH2:1])[S:42][C:41]3=[S:40])[CH:32]=[CH:31]4)[CH:23]=[CH:24][C:25]=2[O:26][CH3:27])[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=1

Participants

6

Reactant 4

HCID 1140TolueneHCID 8082PiperidineHCID 1201546RhodanineHCID 865860406-(3-Phenyl-4-methoxyphenyl)-2-naphthaldehyde

Product 1

HCID 86586041HCID 86586041, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (2.5 mL), piperidine (0.003 mL), acetic acid (0.004 mL), 6-(3-phenyl-4-methoxyphenyl)-2-naphthaldehyde (0.124 g, 0.37 mmol) and 2-thioxo-4-thiazolidinone (0.049 mg, 0.37 mmol) was heated at reflux for 20.5 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in EtOH. After 2 hours, the solid was filtered and dried under high vacuum to afford 0.117 g (70%) of 6-(3-phenyl-4-methoxyphenyl)-naphthalen-2-yl-methylene-2-thioxo4-thiazolidinone, mp 266–269° C. 1H NMR (300 MHz, DMSO-d6): δ 3.82 (s, 3H), 7.25 (d, J=8.4 Hz, 1H), 7.35 (d, J=7.2 Hz, 1H), 7.43 (t, J=7.4 Hz, 2H), 7.57 (d, J=7.2 Hz, 2H), 7.67 (d, J=8.7 Hz, 1H), 7.75 (d, J=2.4 Hz, 1H), 7.77 (s, 1H), 7.84 (dd, J1=6.0 Hz, J2=2.4 Hz, 1H), 7.98 (d, J=8.7 Hz, 1H), 8.10 (t, J=9.0 Hz, 2H), 8.19 (s, 1H), 8.30 (s, 1H), 13.96 (brs, 1H).

Workup

  1. temperatureat reflux for 20.5 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-b2c79fd217ee490581a9e1213e938272
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

Loading…