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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
ノート
印刷プレビュー

反応式

HRID 2226432 の反応式
[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]
参加物実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 176Acetic Acid溶媒
HCID 702
Ethanol
溶媒
HCID 962Water溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0906baa864cd4eb6a565bb2722533a66
出典データセット
uspto-grants-1994_09
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US05348957

反応ノート

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このページの内容参加物実験手順後処理出典と根拠反応ノート