Acetohydroxamic Acid → 4-Fluoro-1,2-benzoxazol-3-amine

HRID 1920716Notes

Reaction equation

HRID 1920716 reaction equation
CC(C)([O-])C.[K+].[C:7]([NH:10][OH:11])(=O)[CH3:8].[F:12][C:13]1C=[CH:19][CH:18]=[C:17](F)[C:14]=1C#N.C[N:23](C)C=O>>[NH2:23][C:7]1[C:8]2[C:13]([F:12])=[CH:14][CH:17]=[CH:18][C:19]=2[O:11][N:10]=1

Participants

5

Reactant 4

HCID 1990Acetohydroxamic AcidHCID 6228DimethylformamideHCID 746952,6-DifluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 166374574-Fluoro-1,2-benzoxazol-3-amine

Procedure

4.00 g (35.65 mmol) of potassium tert-butoxide and 2.60 g (34.64 mmol) of acetohydroxamic acid are dissolved in 50 ml of dry dimethylformamide and stirred at room temperature for 45 minutes. After the addition of 3.30 g (23.72 mmol) of 2,6-difluorobenzonitrile, the mixture is stirred at 50° C. for 16 hours. The mixture is concentrated under reduced pressure, and the residue is dissolved in dichloromethane and washed with water. After drying and concentration of the organic phase, 3.2 g of a yellow resin are obtained, which, according to 1H NMR, is about 85% pure.

Workup

  1. stirringthe mixture is stirred at 50° C. for 16 hours
  2. concentrationThe mixture is concentrated under reduced pressure
  3. dissolutionthe residue is dissolved in dichloromethane
  4. washwashed with water
  5. customAfter drying

Sources & evidence

ORD record
ord-43c645391d1c40b6afb5165efc99b4be
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

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