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2-Acetylfuran → 4-(Furan-2-yl)-1,3-thiazol-2-amine

HRID 1967855
ノート
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反応式

HRID 1967855 の反応式
[C:1]([C:4]1[O:5][CH:6]=[CH:7][CH:8]=1)(=O)[CH3:2].[NH2:9][C:10]([NH2:12])=[S:11]>ClCCl.CO.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC>[NH2:12][C:10]1[S:11][CH:2]=[C:1]([C:4]2[O:5][CH:6]=[CH:7][CH:8]=2)[N:9]=1
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 145052-AcetylfuranHCID 2723790Thiourea

生成物 1

HCID 7278344-(Furan-2-yl)-1,3-thiazol-2-amine収率 20%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 887Methanol溶媒HCID 6344Dichloromethane溶媒

実験手順

2-Acetylfuran (5.1 g, 4.6.0 mmol) was dissolved in a mixed solvent of dichloromethane (50 mL) and methanol (50 mL), and tetra(n-butyl)ammonium bromide (22.3 g, 46.0 mmol) was added thereto, followed by stirring at room temperature for 1 hour. The reaction mixture was concentrated under reduced pressure, water was added to the resulting residue, followed by extraction with ethyl acetate. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was dissolved in acetonitrile (60 mL), thiourea (3.5 g, 46.0 mmol) was added thereto, followed by stirring at room temperature for 30 minutes. The precipitated solid was collected by filtration, and the resulting solid was dissolved in a mixed solvent of a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate, and subjected to liquid-liquid separation. The organic layer was washed with a saturated aqueous solution of sodium chloride and dried over anhydrous magnesium sulfate, and then the solvent was distilled away under reduced pressure. The resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1) to afford 2-amino-4-(2-furyl)thiazole (1.53 g, 20%).

後処理

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated under reduced pressure, water
  3. additionwas added to the resulting residue
  4. extractionfollowed by extraction with ethyl acetate
  5. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  6. dry with materialdried over anhydrous magnesium sulfate
  7. distillationthe solvent was distilled away under reduced pressure
  8. dissolutionThe resulting residue was dissolved in acetonitrile (60 mL)
  9. stirringby stirring at room temperature for 30 minutes
  10. filtrationThe precipitated solid was collected by filtration
  11. dissolutionthe resulting solid was dissolved in a mixed solvent of a saturated aqueous solution of sodium hydrogencarbonate and ethyl acetate
  12. customsubjected to liquid-liquid separation
  13. washThe organic layer was washed with a saturated aqueous solution of sodium chloride
  14. dry with materialdried over anhydrous magnesium sulfate
  15. distillationthe solvent was distilled away under reduced pressure
  16. customThe resulting residue was purified through silica gel column chromatography (hexane:ethyl acetate=3:1)

出典と根拠

ORDレコード
ord-252e5383da5741798da53ed1a6b7c019
出典データセット
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08420827B2

反応ノート

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