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

HRID 74185
Notes
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Reaction equation

HRID 74185 reaction equation
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
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-6875da00e67c46a6a16d50b8bf7dbae0
Source dataset
uspto-grants-2014_09
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08829035B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes