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

HRID 2406171Notes

Reaction equation

HRID 2406171 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-374b95c2071b41a0b81c745671670855
Source dataset
uspto-grants-2014_08
Patent number
US08809353B2

Reaction notes

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