Water → 1,2-Benzoxazol-3-amine

HRID 2262873Notes

Reaction equation

HRID 2262873 reaction equation
C([NH:4]O)(=O)C.CC(C)([O-])C.[K+].F[C:13]1[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16].[OH2:21]>CN(C)C=O>[O:21]1[C:13]2[CH:20]=[CH:19][CH:18]=[CH:17][C:14]=2[C:15]([NH2:4])=[N:16]1

Participants

6

Reactant 4

HCID 962WaterHCID 1990Acetohydroxamic AcidHCID 678552-FluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 27797491,2-Benzoxazol-3-amineYield 27%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of acetohydroxamic acid (10.0 g, 133 mmol) in N,N-dimethylformamide (150 ml) was added potassium tert-butoxide (14.9 g, 133 mmol), and the mixture was stirred at room temperature for 30 minutes. 2-Fluorobenzonitrile (18.0 g, 133 mmol) was added thereto, followed by stirring at room temperature for 5 hours. The reaction mixture was poured to water and extracted with ethyl acetate. The extract was washed with water and dried over anhydrous magnesium sulfate, and the solvent was distilled off under reduced pressure. The residue was recrystallized from hexane to give 4.80 g (27.0%) of the desired product as a solid.

Workup

  1. stirringby stirring at room temperature for 5 hours
  2. extractionextracted with ethyl acetate
  3. washThe extract was washed with water
  4. dry with materialdried over anhydrous magnesium sulfate
  5. distillationthe solvent was distilled off under reduced pressure
  6. customThe residue was recrystallized from hexane

Sources & evidence

ORD record
ord-f065078cb22b432bb65b8cd457a3a6a2
Source dataset
uspto-grants-2010_12
Patent number
US07851473B2

Reaction notes

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