Triethylamine → 5-(Benzoxazol-2-yl)-2-(tetrahydropyran-4-yl)nitrobenzene

HRID 74185

反応式

HRID 74185 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-6875da00e67c46a6a16d50b8bf7dbae0
出典データセット
uspto-grants-2014_09
特許番号
US08829035B2

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