Toluene → HCID 86586037, compound

HRID 860548Notes

Reaction equation

HRID 860548 reaction equation
C1(C)C=CC=CC=1.N1CCCCC1.[C:14]12([C:24]3[CH:25]=[C:26]([C:38]4[C:43]([CH:44]=O)=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:27]=[CH:28][C:29]=3[O:30][Si:31]([C:34]([CH3:37])([CH3:36])[CH3:35])([CH3:33])[CH3:32])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2.[S:46]1[CH2:50][C:49](=[O:51])[NH:48][C:47]1=[O:52]>C(O)(=O)C>[C:14]12([C:24]3[CH:25]=[C:26]([C:38]4[C:43]([CH:44]=[C:50]5[S:46][C:47](=[O:52])[NH:48][C:49]5=[O:51])=[CH:42][CH:41]=[CH:40][CH:39]=4)[CH:27]=[CH:28][C:29]=3[O:30][Si:31]([C:34]([CH3:35])([CH3:36])[CH3:37])([CH3:32])[CH3:33])[CH2:23][CH:18]3[CH2:19][CH:20]([CH2:22][CH:16]([CH2:17]3)[CH2:15]1)[CH2:21]2

Participants

6

Reactant 4

HCID 1140TolueneHCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 86586038HCID 86586038, compound

Product 1

HCID 86586037HCID 86586037, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

A solution of toluene (10 mL), piperidine (0.04 mL), acetic acid (0.04 mL), 6-[3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzaldehyde (0.473 g, 1.06 mmol) and 2,4-thiazolidinedione (0.125 mg, 1.06 mmol) was heated at reflux for 23 hours under an argon atmosphere. The resulting suspension was filtered and the solid was stirred at room temperature in 30 mL of EtOH. After 20 minutes, the solid was filtered and dried under high vacuum to afford 0.400 g (70%) of 6-[3-(1-adamantyl)-4-(t-butyldimethylsilyloxy)phenyl]-benzylidene-2,4-thiazolidinedione, mp 277–278° C. 1H NMR (300 MHz, DMSO-d6): δ 0.33 (s, 6H), 1.00 (s, 9H), 1.72 (brs, 6H), 2.01–2.09 (m, 9H), 6.89 (d, J=7.8 Hz, 1H), 7.42–7.44 (m, 2H), 7.61 (d, J=8.4 Hz, 2H), 7.73 (d, J=8.4 Hz, 2H), 7.79 (s, 1H), 12.60 (brs, 1H); 13C NMR (75 MHz, DMSO-d6): ppm −3.6, 18.6, 26.1, 28.4, 36.5, 119.2, 122.5, 125.0, 125.4, 126.6, 130.5, 130.9, 131.0, 131.3, 139.0, 142.0, 154.4, 167.2, 167.6.

Workup

  1. temperatureat reflux for 23 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-16ed154984604b648e0045809a5f9fab
Source dataset
uspto-grants-2006_12
Patent number
US07153875B2

Reaction notes

Loading…