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

HRID 2949
Notes
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Reaction equation

HRID 2949 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]
ParticipantsProcedureSources & evidenceReaction notes

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 liter 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-0c27d491eec04e228dfd3d1e3bf80bcf
Source dataset
uspto-grants-1998_03
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US05731336

Reaction notes

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On this pageParticipantsProcedureSources & evidenceReaction notes