Sodium Acetate → 5-[(3,5-Di-2-propenyl-4-hydroxyphenyl)-methylene]-2-thioxo-4-thiazolidinone

HRID 2295073

Reaction equation

HRID 2295073 reaction equation
[CH2:1]([C:4]1[CH:5]=[C:6]([CH:9]=[C:10]([CH2:13][CH:14]=[CH2:15])[C:11]=1[OH:12])[CH:7]=O)[CH:2]=[CH2:3].[S:16]1[CH2:22][C:20](=[O:21])[NH:19][C:17]1=[S:18].C([O-])(=O)C.[Na+]>C(O)(=O)C>[CH2:1]([C:4]1[CH:5]=[C:6]([CH:7]=[C:22]2[S:16][C:17](=[S:18])[NH:19][C:20]2=[O:21])[CH:9]=[C:10]([CH2:13][CH:14]=[CH2:15])[C:11]=1[OH:12])[CH:2]=[CH2:3]

Participants

5

Reactant 3

HCID 517045Sodium AcetateHCID 1201546RhodanineHCID 120477783,5-Di-(2-propenyl)-4-hydroxybenzaldehyde

Product 1

HCID 540052885-[(3,5-Di-2-propenyl-4-hydroxyphenyl)-methylene]-2-thioxo-4-thiazolidinoneYield 94.6%

Reagents, catalysts & solvents 1

HCID 176Acetic AcidSolvent

Procedure

3,5-di-(2-propenyl)-4-hydroxybenzaldehyde (50.5 g), 36.6 g of rhodanine and 164 g of sodium acetate were heated together at reflux temperature in 1.25 liter of acetic acid for 14.5 hours. The resultant solution was cooled, poured into 2 l of ice water to yield, upon separation, about 75 g of 5-[(3,5-di-2-propenyl-4-hydroxyphenyl)methylene]-2-thioxo-4-thiazolidinone, m.p. 157°-160° C.

Sources & evidence

ORD record
ord-9ce11ec954b84df5873e6eb5f1d30ca8
Source dataset
uspto-grants-1997_11
Patent number
US05691367

Linked notes

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