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

HRID 2226432
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HRID 2226432 반응식
[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]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 3

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

생성물 1

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

시약·촉매·용매 3

HCID 176Acetic Acid용매
HCID 702
Ethanol
용매
HCID 962Water용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-0906baa864cd4eb6a565bb2722533a66
출처 데이터셋
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US05348957

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