Benzaldehyde → 5-[[4-[(4-Decanoyl-3-hydroxy-2-propylphenoxy)methyl]phenyl]methylene]-2-thioxo-4-thiazolidinone

HRID 1289173Notes

Reaction equation

HRID 1289173 reaction equation
[C:1]([C:12]1[CH:27]=[CH:26][C:15]([O:16][CH2:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=O)=[CH:20][CH:19]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[C:13]=1[OH:31])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10].[S:32]1[CH2:38][C:36](=[O:37])[NH:35][C:33]1=[S:34].C(=O)C1C=CC=CC=1.C([O-])(=O)C.[Na+]>C(O)(=O)C>[C:1]([C:12]1[CH:27]=[CH:26][C:15]([O:16][CH2:17][C:18]2[CH:25]=[CH:24][C:21]([CH:22]=[C:38]3[S:32][C:33](=[S:34])[NH:35][C:36]3=[O:37])=[CH:20][CH:19]=2)=[C:14]([CH2:28][CH2:29][CH3:30])[C:13]=1[OH:31])(=[O:11])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6][CH2:7][CH2:8][CH2:9][CH3:10]

Participants

6

Reactant 4

HCID 240BenzaldehydeHCID 517045Sodium AcetateHCID 1201546Rhodanine2×HCID 211912474-[(4-Decanoyl-3-hydroxy-2-propylphenoxy)methyl]benzaldehyde

Product 1

HCID 867525175-[[4-[(4-Decanoyl-3-hydroxy-2-propylphenoxy)methyl]phenyl]methylene]-2-thioxo-4-thiazolidinoneYield 84%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

The 4-[(4-decanoyl-3-hydroxy-2-propylphenoxy)methyl]benzaldehyde thus obtained was coupled with the rhodanine by reacting equimolar amounts of the benzaldehyde and the rhodanine in the presence of sodium acetate and acetic acid as previously described to yield 1.6 g (84%) of the title product. mp 187.5°-188° C.

Sources & evidence

ORD record
ord-eb48911af1234711b90eb155eab65fba
Source dataset
uspto-grants-1998_05
Patent number
US05747517

Reaction notes

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