4-Thiazolidinone, 3-methyl-2-thioxo- → 5-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-3-methyl-2-thioxo-4-thiazolidinone

HRID 2226433Notes

Reaction equation

HRID 2226433 reaction equation
[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:15])([CH3:14])[CH3:13])[N:8]=[C:7]([CH:16]=O)[N:6]=1)([CH3:4])[CH3:3].C([O-])(=O)C.[Na+].[CH3:23][N:24]1[C:28](=[O:29])[CH2:27][S:26][C:25]1=[S:30]>C(O)(=O)C.C(O)C.O>[CH3:13][C:12]([C:9]1[C:10]([OH:11])=[C:5]([C:2]([CH3:3])([CH3:1])[CH3:4])[N:6]=[C:7]([CH:16]=[C:27]2[S:26][C:25](=[S:30])[N:24]([CH3:23])[C:28]2=[O:29])[N:8]=1)([CH3:14])[CH3:15]

Participants

7

Reactant 3

HCID 729004-Thiazolidinone, 3-methyl-2-thioxo-HCID 517045Sodium AcetateHCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

Product 1

HCID 544480905-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-3-methyl-2-thioxo-4-thiazolidinoneYield 47%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (0.50 g, 2.1 mmol), sodium acetate (0.60 g, 7.3 mmol), and 3-methylrhodanine (0.31 g, 2.1 mmol) in glacial acetic acid (10 mL) is placed under nitrogen atmosphere and warmed to reflux. After refluxing 21 hours, the mixture is cooled to room temperature and diluted with a 1:1 mixture of ethanol and water. The resulting slurry is stirred 0.5 hours and filtered. The precipitate is recrystallized from methanol and water to give 0.36 g (47%) of the title compound, mp 226°-228° C.

Workup

  1. temperaturewarmed to reflux
  2. temperatureAfter refluxing 21 hours
  3. filtrationfiltered
  4. customThe precipitate is recrystallized from methanol and water

Sources & evidence

ORD record
ord-fb0f4bda0a9144a2a4daf945793a15a7
Source dataset
uspto-grants-1994_09
Patent number
US05348957

Reaction notes

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