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

HRID 2226432Notes

Reaction equation

HRID 2226432 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+].[NH2:23][N:24]1[C:28](=[O:29])[CH2:27][S:26][C:25]1=[S:30]>C(O)(=O)C.C(O)C.O>[CH3:1][C:2]([C:5]1[C:10]([OH:11])=[C:9]([C:12]([CH3:14])([CH3:15])[CH3:13])[N:8]=[C:7]([CH:16]=[C:27]2[S:26][C:25](=[S:30])[N:24]([NH2:23])[C:28]2=[O:29])[N:6]=1)([CH3:3])[CH3:4]

Participants

7

Reactant 3

HCID 740333-AminorhodanineHCID 517045Sodium AcetateHCID 152948964,6-Di-tert-butyl-5-hydroxypyrimidine-2-carbaldehyde

Product 1

HCID 545175845-[[4,6-Bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidinyl]methylene]-3-amino-2-thioxo-4-thiazolidinoneYield 27.1%

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4,6-bis(1,1-dimethylethyl)-5-hydroxy-2-pyrimidine carboxaldehyde (1.00 g, 4.23 mmol), sodium acetate (1.36 g, 16.6 mmol), and 3-aminorhodanine (0.63 g, 4.3 mmol) in glacial acetic acid (15 mL), under nitrogen atmosphere, is warmed to reflux and refluxed 7 hours. This mixture is then cooled to room temperature and stirred 16 hours. After stirring, the reaction mixture is diluted with a 1:2 mixture of ethanol and water and extracted with ethyl acetate. The combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine. The organic phase is dried over magnesium sulfate, concentrated, and purified by flash chromatography (SiO2, 20% ethyl acetate/hexane) followed by recrystallization from methanol and water to give 0.42 g (27%) of the title compound, mp 194°-196° C.

Workup

  1. temperatureunder nitrogen atmosphere, is warmed
  2. temperatureto reflux
  3. temperaturerefluxed 7 hours
  4. stirringAfter stirring
  5. extractionextracted with ethyl acetate
  6. washThe combined organic extracts are washed with water, aqueous 0.2N hydrochloric acid solution, and brine
  7. dry with materialThe organic phase is dried over magnesium sulfate
  8. concentrationconcentrated
  9. custompurified by flash chromatography (SiO2, 20% ethyl acetate/hexane)
  10. customfollowed by recrystallization from methanol and water

Sources & evidence

ORD record
ord-0906baa864cd4eb6a565bb2722533a66
Source dataset
uspto-grants-1994_09
Patent number
US05348957

Reaction notes

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