Thiazolidinedione → 5-[4-(3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl)phenylmethylene]thiazolidine-2,4-dione
Reaction equation
[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:24]=[CH:23][C:20]([CH:21]=O)=[CH:19][CH:18]=1)=[O:16].[S:25]1[CH2:29][C:28](=[O:30])[NH:27][C:26]1=[O:31].N1CCCCC1>>[CH3:1][C:2]1[O:6][C:5]([C:7]2[CH:8]=[CH:9][CH:10]=[CH:11][CH:12]=2)=[N:4][C:3]=1[CH2:13][CH2:14][C:15]([C:17]1[CH:18]=[CH:19][C:20]([CH:21]=[C:29]2[S:25][C:26](=[O:31])[NH:27][C:28]2=[O:30])=[CH:23][CH:24]=1)=[O:16]Participants
4
Procedure
4-[3-(5-Methyl-2-phenyl-4-oxazolyl)propionyl]benzaldehyde, the title product of Preparation 4, (16 g, 0.05 mol), thiazolidine-2,4-dione (11.7 g, 0.10 mol and piperidine (0.85 g, 0.01 mol) were combined in 300 mL absolute ethanol, and the mixture refluxed for 24 hours, cooled to 0° C., diluted slowly with 600 mL of ether and, after stirring for 1 hour at 0° C., crude product recovered by filtration. The crude product was triturated with 150 mL of warm acetic acid (40°-50° C.). The resulting slurry was cooled to room temperature, diluted with 300 mL of ether, and 14.2 g (71%) of purified title product recovered by filtration; mp 224°-225° C.
Sources & evidence
- ORD record
- ord-1696f9d6a80d45d0addd5ed9094497e0
- Source dataset
- uspto-grants-1992_07
- Patent number
- US05130379
Reaction notes
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