Acetohydroxamic Acid → HCID 58267696, compound

HRID 1920717Notes

Reaction equation

HRID 1920717 reaction equation
CC(C)([O-])C.[K+].C([NH:10][OH:11])(=O)C.[F:12][CH:13]([F:24])[O:14][C:15]1[CH:22]=[CH:21][CH:20]=[C:19](F)[C:16]=1[C:17]#[N:18]>CN(C)C=O>[NH2:18][C:17]1[C:16]2[C:15]([O:14][CH:13]([F:24])[F:12])=[CH:22][CH:21]=[CH:20][C:19]=2[O:11][N:10]=1

Participants

5

Reactant 3

HCID 1990Acetohydroxamic AcidHCID 234483612-(Difluoromethoxy)-6-fluorobenzonitrileHCID 23665647Potassium tert-butoxide

Product 1

HCID 58267696HCID 58267696, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

8.00 g (71.29 mmol) of potassium tert-butoxide and 5.20 g (69.27 mmol) of acetohydroxamic acid are dissolved in 50 ml of dry dimethylformamide and stirred at room temperature for 1 hour. After the addition of 4.40 g (23.51 mmol) of 2-(difluoromethoxy)-6-fluorobenzonitrile, the mixture is stirred first at room temperature for 3 hours and then at 60° C. for 16 hours. The mixture is concentrated under reduced pressure, the residue is stirred with water and the pale olive-coloured precipitate is filtered off with suction. This gives 4.4 g of product, which, according to LC-MS, is about 89% pure.

Workup

  1. stirringthe mixture is stirred first at room temperature for 3 hours
  2. waitat 60° C. for 16 hours
  3. concentrationThe mixture is concentrated under reduced pressure
  4. stirringthe residue is stirred with water
  5. filtrationthe pale olive-coloured precipitate is filtered off with suction

Sources & evidence

ORD record
ord-cdd77e06ea6744839150a15d9cc92a2d
Source dataset
uspto-grants-2012_05
Patent number
US08173641B2

Reaction notes

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