P-Anisidine → 2-(4-(4-Methoxyphenylamino)-3-nitrophenyl)benzoxazole

HRID 74175

Reaction equation

HRID 74175 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(=O)([O-])O.[Na+].[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH2:33])=[CH:29][CH:28]=1>C(O)C>[CH3:25][O:26][C:27]1[CH:32]=[CH:31][C:30]([NH:33][C:2]2[CH:7]=[CH:6][C:5]([C:8]3[O:9][C:10]4[CH:16]=[CH:15][CH:14]=[CH:13][C:11]=4[N:12]=3)=[CH:4][C:3]=2[N+:17]([O-:19])=[O:18])=[CH:29][CH:28]=1

Participants

5

Reactant 3

HCID 7732P-AnisidineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674982092-(4-(4-Methoxyphenylamino)-3-nitrophenyl)benzoxazoleYield 86%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a suspension of 2-(4-fluoro-3-nitrophenyl)benzoxazole (see Working Example 15-2) (300 mg, 1.19 mmol) in ethanol (5 mL) was added sodium hydrogen carbonate (295 mg, 2.32 mmol) and p-anisidine (357 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, the precipitated crystals were filtered off, and after washing with water and ethanol the crystals were dried to yield the title compound (359 mg, 86% yield) as orange crystals.

Workup

  1. temperaturethis was heated
  2. temperatureto reflux
  3. filtrationthe precipitated crystals were filtered off
  4. washafter washing with water and ethanol the crystals
  5. customwere dried

Sources & evidence

ORD record
ord-971270a2eab341f2963d927eae88f57b
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

Loading…