Water → 2-(4-Benzylamino-3-nitrophenyl)benzoxazole

HRID 74179

Reaction equation

HRID 74179 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+].[CH2:25]([NH2:32])[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.O>C(O)C>[CH2:25]([NH:32][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:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1

Participants

6

Reactant 4

HCID 962WaterHCID 7504BenzylamineHCID 516892Sodium BicarbonateHCID 219909702-(4-Fluoro-3-nitrophenyl)benzoxazole

Product 1

HCID 674986602-(4-Benzylamino-3-nitrophenyl)benzoxazoleYield 84.4%

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 (195 mg, 2.32 mmol) and benzylamine (311 mg, 2.90 mmol), and this was heated to reflux with stirring for 4 hours. After the reaction was complete, it was cooled to room temperature and water was added. The precipitated crystals were filtered off, and after washing with water and ethanol the crystals were dried to yield the title compound (347 mg, 84% 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-dd0cd11f2a004dd195fc4e3c5e347ac5
Source dataset
uspto-grants-2014_09
Patent number
US08829035B2

Linked notes

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