Tert-Butylamine → 2-(2-Tert-butylaminoanilin-5-yl)benzoxazole

HRID 74196Notes

Reaction equation

HRID 74196 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-])=O.C(=O)([O-])O.[Na+].[C:25]([NH2:29])([CH3:28])([CH3:27])[CH3:26].[H][H]>C(O)C.[C].[Pd].O1CCCC1.O>[C:25]([NH:29][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[NH2:17])([CH3:28])([CH3:27])[CH3:26]

Participants

9

Reactant 4

HCID 6385Tert-ButylamineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazoleHCID 178418361HCID 178418361, compound

Product 1

HCID 674984142-(2-Tert-butylaminoanilin-5-yl)benzoxazoleYield 19%

Reagents, catalysts & solvents 4

HCID 178418390HCID 178418390, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.16 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (195 mg, 2.32 mmol) and tert-butylamine (212 mg, 2.90 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, this was cooled to room temperature, water was added, and this was extracted with chloroform. After the organic layer obtained was dried over anhydrous sodium sulfate, it was filtered and concentrated. The crystals obtained were added to a tetrahydrofuran (5 mL) solution containing 10% palladium-carbon (50 mg), a hydrogen atmosphere was substituted in the flask and this was stirred at room temperature for 8 hours. After the reaction was complete, this was filtered through Celite and the filtrate was concentrated. The residue obtained was purified by silica gel column chromatography to yield the title compound (50.1 mg, 19% yield) as red crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. extractionthis was extracted with chloroform
  4. customAfter the organic layer obtained
  5. dry with materialwas dried over anhydrous sodium sulfate, it
  6. filtrationwas filtered
  7. concentrationconcentrated
  8. customThe crystals obtained
  9. stirringthis was stirred at room temperature for 8 hours
  10. filtrationthis was filtered through Celite
  11. concentrationthe filtrate was concentrated
  12. customThe residue obtained
  13. customwas purified by silica gel column chromatography

Sources & evidence

ORD record
ord-8316ccb7b43d4b00be5e68108db37b62
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Reaction notes

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