Toluene → 4-[3-(1-Adamantyl)-4-methoxyphenyl]benzylidene-2,4-thiazolidinedione

HRID 860536Notes

Reaction equation

HRID 860536 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:39]=[CH:38][C:35]([CH:36]=O)=[CH:34][CH:33]=4)[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:40]1[CH2:44][C:43](=[O:45])[NH:42][C:41]1=[O:46]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:32]4[CH:39]=[CH:38][C:35]([CH:36]=[C:44]5[S:40][C:41](=[O:46])[NH:42][C:43]5=[O:45])=[CH:34][CH:33]=4)[CH:27]=[CH:28][C:29]=3[O:30][CH3:31])[CH2:21][CH:20]3[CH2:19][CH:18]([CH2:17][CH:16]([CH2:22]3)[CH2:15]1)[CH2:23]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 865860334-[3-(1-Adamantyl)-4-methoxyphenyl]benzaldehyde

Product 1

HCID 724165724-[3-(1-Adamantyl)-4-methoxyphenyl]benzylidene-2,4-thiazolidinedioneYield 87%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (6 mL), piperidine (10 μL), acetic acid (10 μL), 4-[3-(1-adamantyl)-4-methoxyphenyl]benzaldehyde (0.337 g, 0.97 mmol) and 2,4-thiazolidinedione (0.114 g, 0.97 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 toluene and ethanol. The yellow solid was dried under high vacuum to afford 0.375 g (87%) of 4-[3-(1-adamantyl)-4-methoxyphenyl]benzylidene-2,4-thiazolidinedione, mp 304–306° C. 1H NMR (300 MHz; DMSO-d6): 1.75 (s, 6H), [2.06 (s), 2.11 (s), 9 H], 3.85 (s, 3H), 7.09 (d, J=8.7 Hz, 1H), 7.46 (d, J=2.3 Hz, 1H), 7.57 (dd, J=8.7 Hz, J=2.3 Hz, 1H), 7.65 (d, J=8.4 Hz, 2H), 7.80 (d, J=8.4 Hz, 2H), 7.82 (s, 1H), 12.4–12.7 (brs, 1H).

Workup

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

Sources & evidence

ORD record
ord-afb474fbee054769b71ebc458be2c3b5
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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