Thiazolidinedione → 5-[(3,4-Dihydroxy-5-chlorophenyl)methylidene]-thiazolidin-2,4-dione

HRID 2379414

Reaction equation

HRID 2379414 reaction equation
[S:1]1[CH2:5][C:4](=[O:6])[NH:3][C:2]1=[O:7].[OH:8][C:9]1[CH:10]=[C:11]([CH:14]=[C:15]([Cl:18])[C:16]=1[OH:17])[CH:12]=O.N1CCCCC1>C(O)(=O)C>[OH:8][C:9]1[CH:10]=[C:11]([CH:12]=[C:5]2[S:1][C:2](=[O:7])[NH:3][C:4]2=[O:6])[CH:14]=[C:15]([Cl:18])[C:16]=1[OH:17]

Participants

5

Reactant 3

HCID 5437ThiazolidinedioneHCID 8082PiperidineHCID 24681823-Chloro-4,5-dihydroxybenzaldehyde

Product 1

HCID 540303995-[(3,4-Dihydroxy-5-chlorophenyl)methylidene]-thiazolidin-2,4-dione

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Conditions

Temperature
100 °C

Procedure

A solution containing 1.33 g of thiazolidine-2,4-dione, 1.72 g of 3,4-dihydroxy-5-chlorobenzaldehyde and 2 ml of piperidine in 20 ml of acetic acid was heated for five hours at 100 ° C. Yield 1.9 g (70%), mp 299°-301° C.

Sources & evidence

ORD record
ord-9280142cdc7148eea86c11a532dbd818
Source dataset
uspto-grants-1994_11
Patent number
US05362733

Linked notes

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