Thiazolidinedione → HCID 54512542, compound

HRID 1729048Notes

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][NH:14]C1(C)CCC2C(C)(C)C2(C2C=CC(C=O)=CC=2)C1=O.[S:34]1[CH2:38][C:37](=[O:39])[NH:36][C:35]1=[O:40].[C:41]([O-:44])(=O)[CH3:42].[Na+]>>[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][NH:14][C:41](=[O:44])[C:42]1[CH:11]=[CH:12][C:7]([CH:5]=[C:38]2[S:34][C:35](=[O:40])[NH:36][C:37]2=[O:39])=[CH:8][CH:9]=1

Participants

Reactant 3

HCID 5437Thiazolidinedione

HCID 517045Sodium Acetate

HCID 86747985HCID 86747985, compound

Product 1

HCID 54512542HCID 54512542, compound

Procedure

4-[(5-Methyl-2-phenyl-4-oxazolyl)methylaminocaronyl]benzaldehyde (0.880 g, 2.75 mmol), thiazolidine-2,4-dione (0.483 g, 4.12 mmol) and sodium acetate(0.676 g, 8.24 mmol) were intimately mixed and heated at 140°-145° C. for 45 minutes, then cooled to room temperature, the solids triturated and stirred with mL of water for 30 minutes and 1.20 g of present title product recovered by filtration; mp 235°-237° C. (dec); tlc Rf 0.2 (3:1 ethyl acetate:hexane).

Workup

temperatureheated at 140°-145° C. for 45 minutes
customthe solids triturated
filtration1.20 g of present title product recovered by filtration

Sources & evidence

ORD record: ord-8848854f5e634cf0a662016975fdd49a
Source dataset: uspto-grants-1994_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US05330998

Reaction notes

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