Toluene → HCID 72416571, compound

HRID 860538Notes

Reaction equation

HRID 860538 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:31]4[CH:38]=[CH:37][C:34]([CH:35]=O)=[CH:33][CH:32]=4)[CH:27]=[CH:28][C:29]=3[OH:30])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[S:39]1[CH2:43][C:42](=[O:44])[NH:41][C:40]1=[O:45]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:31]4[CH:38]=[CH:37][C:34]([CH:35]=[C:43]5[S:39][C:40](=[O:45])[NH:41][C:42]5=[O:44])=[CH:33][CH:32]=4)[CH:27]=[CH:28][C:29]=3[OH:30])[CH2:15][CH:16]3[CH2:17][CH:18]([CH2:19][CH:20]([CH2:22]3)[CH2:21]1)[CH2:23]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 11244477HCID 11244477, compound

Product 1

HCID 72416571HCID 72416571, compoundYield 71%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (180 mL), piperidine (0.60 mL), acetic acid (0.63 mL), 4-[3-(1-adamantyl)-4-hydroxyphenyl]benzaldehyde (6.08 g, 18.30 mmol) and 2,4-thiazolidinedione (2.14 g, 18.30 mmol) was heated at reflux for 12 hours under an argon atmosphere. The resulting suspension was filtered hot and the solid was stirred at room temperature in 210 mL of H2O/EtOH (6:1). After 30 minutes the solid was filtered and dried under high vacuum to afford 5.6 g (71%) of 4-[3-(1-adamantyl)-4-hydroxyphenyl]benzylidene-2,4-thiazolidinedione, mp 307–308.5° C. 1H NMR (300 MHz; DMSO-d6): δ 1.75 (brs, 6H), 2.05–2.13 (m, 9H), 6.88 (dd, J1=1.8 Hz, J2=8.7 Hz, 1H), 7.40–7.42 (m, 2H), 7.61–7.64 (m, 2H), 7.73–7.79 (m, 3H), 9.62 (s, 1H), 12.57 (brs, 1H).

Workup

  1. temperatureat reflux for 12 hours under an argon atmosphere
  2. filtrationThe resulting suspension was filtered hot
  3. filtrationAfter 30 minutes the solid was filtered
  4. customdried under high vacuum

Sources & evidence

ORD record
ord-b824e73e112949878b7f5f67ec1169a1
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

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