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

HRID 1361879
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HRID 1361879 반응식
[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
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참가 물질

6

반응물 2

HCID 145052-AcetylfuranHCID 2723790Thiourea

생성물 1

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

시약·촉매·용매 3

HCID 74236Tetrabutylammonium Bromide촉매HCID 887Methanol용매HCID 6344Dichloromethane용매

실험 절차

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%).

후처리

  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)

출처 및 근거

ORD 기록
ord-ff614292210942439f7910ef8a362f01
출처 데이터셋
uspto-grants-2011_02
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07880013B2

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