三乙胺 → 5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)nitrobenzene

HRID 74185

反应方程式

HRID 74185 反应方程式
F[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[O:9][C:10]3[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=3[N:12]=2)=[CH:4][C:3]=1[N+:17]([O-:19])=[O:18].C(N(CC)CC)C.N[CH:28]1[CH2:33][CH2:32][CH2:31][CH2:30][O:29]1>C(O)C>[O:9]1[C:10]2[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=2[N:12]=[C:8]1[C:5]1[CH:6]=[CH:7][C:2]([CH:32]2[CH2:31][CH2:30][O:29][CH2:28][CH2:33]2)=[C:3]([N+:17]([O-:19])=[O:18])[CH:4]=1

参与物

5

反应物 3

HCID 8471三乙胺HCID 14471248Oxan-2-amineHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

产物 1

HCID 674981085-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)nitrobenzene收率 63.7%

试剂、催化剂与溶剂 1

HCID 702乙醇溶剂

实验过程

5-(Benzoxazol-2-yl)-2-fluoronitrobenzene (see Working Example 15-2) (0.55 g, 2.13 mmol), triethylamine (0.26 g, 2.57 mmol), and aminotetrahydropyran (0.24 g, 2.34 mmol) were added to ethanol (10 mL), and this reaction mixture liquid was heated to reflux with stirring for 2 hours. The reaction mixture was cooled to room temperature and was concentrated under reduced pressure, and 0.1N aqueous hydrochloric acid solution (50 mL) was added to the residue obtained, this was successively extracted with ethyl acetate (approx. 50 mL, 4 times), washed with water (30 mL), and dried over anhydrous sodium sulfate, and the solvent was distilled off at reduced pressure. The residue obtained was purified by silica gel column chromatography to yield the title compound (440 mg, 60.9% yield) as light brown crystals.

后处理

  1. temperaturethis reaction mixture liquid was heated
  2. temperatureto reflux
  3. concentrationwas concentrated under reduced pressure, and 0.1N aqueous hydrochloric acid solution (50 mL)
  4. additionwas added to the residue
  5. customobtained
  6. extractionthis was successively extracted with ethyl acetate (approx. 50 mL, 4 times)
  7. washwashed with water (30 mL)
  8. dry with materialdried over anhydrous sodium sulfate
  9. distillationthe solvent was distilled off at reduced pressure
  10. customThe residue obtained
  11. customwas purified by silica gel column chromatography

来源与证据

ORD记录
ord-6875da00e67c46a6a16d50b8bf7dbae0
来源数据集
uspto-grants-2014_09
专利号
US08829035B2

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