Hydrochloric Acid → (2E)-N-(4-Fluorophenyl)-2-(hydroxyimino)acetamide

HRID 2062159Notes

Reaction equation

HRID 2062159 reaction equation
[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[CH:4][CH:3]=1.Cl.Cl[C:11](Cl)(Cl)[CH:12]([OH:14])O.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:25][OH:26]>O>[F:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:12](=[O:14])/[CH:11]=[N:25]/[OH:26])=[CH:4][CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 97314-FluoroanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6869015(2E)-N-(4-Fluorophenyl)-2-(hydroxyimino)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
100 °C

Procedure

4-Fluoroaniline (58.2 g, 0.50 mol) was added slowly to 10% aqueous HCl solution. This suspension was added to a mixture of chloral hydrate (95 g, 0.55 mol) and sodium sulfate (0.5 kg) in 750 mL water with mechanical stirring. Hydroxylamine hydrochloride (116 g, 1.63 mol) dissolved in water (250 mL) was added, and the resulting slurry was heated at 100° C. After this temperature was reached, the heating mantle was removed immediately, and the solution was cooled to room temperature. The formed precipitate was collected by filtration, washed with water (2×300 mL), and dried in a vacuum oven at 60° C. Yield: 78.2 g of N-(4-fluorophenyl)-2-hydroxyiminoacetamide as an off-white solid.

Workup

  1. additionwas added
  2. customthe heating mantle was removed immediately
  3. temperaturethe solution was cooled to room temperature
  4. filtrationThe formed precipitate was collected by filtration
  5. washwashed with water (2×300 mL)
  6. customdried in a vacuum oven at 60° C

Sources & evidence

ORD record
ord-619de755969a49a2899df72c4928a858
Source dataset
uspto-grants-2012_10
Patent number
US08283354B2

Reaction notes

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