Toluene → HCID 72416577, compound

HRID 860531Notes

Reaction equation

HRID 860531 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:23]=[C:24]([C:31]2[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=2)[CH:25]=[C:26]2[O:30][CH2:29][O:28][C:27]=12.[S:39]1[CH2:43][C:42](=[O:44])[NH:41][C:40]1=[O:45]>C(O)(=O)C>[CH3:14][O:15][C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=1[C:22]1[CH:23]=[C:24]([C:31]2[CH:32]=[CH:33][C:34]([CH:35]=[C:43]3[S:39][C:40](=[O:45])[NH:41][C:42]3=[O:44])=[CH:37][CH:38]=2)[CH:25]=[C:26]2[O:30][CH2:29][O:28][C:27]=12

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86586030HCID 86586030, compound

Product 1

HCID 72416577HCID 72416577, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (10 mL), piperidine (10 μL), acetic acid (10 μL), 4-[3-(2-methoxyphenyl)-4,5-methylenedioxyphenyl]benzaldehyde (0.164 g, 0.493 mmol) and 2,4-thiazolidinedione (0.0578 g, 0.493 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 ethanol. The yellow solid was dried under high vacuum to afford 0.125 g (59%) of 4-[3-(2-methoxyphenyl)-4,5-methylenedioxyphenyl]-benzylidene-2,4-thiazolidinedione, mp 227–228° C. (dec.). 1H NMR (300 MHz; DMSO-d6): 3.77 (s, 3H), 6.05 (s, 2H), 7.12 (t, J=7.5 Hz, 1H), 7.12 (d, J=8.7 Hz, 1H), 7.23 (s, 1H), 7.30 (s, 1H), 7.33–7.43 (m, 2H), 7.63 (d, J=7.8 Hz, 2H), 7.80 (d, J=7.8 Hz, 2H), 7.81 (s, 1H), 12.5–12.7 (brs, 1H). 13C NMR (75 MHz; DMSO-d6): 56.3, 56.4, 101.9, 106.6, 112.4, 120.8, 121.0, 123.0, 123.6, 124.7, 127.8, 130.2, 131.3, 131.4, 132.0, 132.2, 133.1, 142.2, 145.9, 148.7, 157.1, 168.0, 168.4.

Workup

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

Sources & evidence

ORD record
ord-f3fb25d5b7224fabaebe6a1014581f92
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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