Chloral → N-(3,5-Dichlorophenyl)-2-(hydroxyimino)acetamide

HRID 1603718Notes

Reaction equation

HRID 1603718 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:6]=[C:7]([Cl:9])[CH:8]=1)[NH2:5].[O:10]=[CH:11][C:12](Cl)(Cl)Cl.[O-]S([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:24][OH:25]>O.Cl.O1CCOCC1>[Cl:1][C:2]1[CH:3]=[C:4]([NH:5][C:11](=[O:10])[CH:12]=[N:24][OH:25])[CH:6]=[C:7]([Cl:9])[CH:8]=1

Participants

8

Reactant 4

HCID 6407ChloralHCID 122813,5-DichloroanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 71353147N-(3,5-Dichlorophenyl)-2-(hydroxyimino)acetamideYield 89%

Reagents, catalysts & solvents 3

HCID 313Hydrochloric AcidSolventHCID 962WaterSolvent3×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
50 °C

Procedure

A mixture of 3,5-dichloroaniline (10.0 g, 61.7 mmol) in H2O(50 mL), concentrated HCl(12 mL) and 1,4-dioxane (20 mL) was heated to be clear solution, and then added to a mixture of chloral hydrated (10.5 g, 66.9 mmol) and Na2SO4 (66.0 g) in H2O (224 mL) which has been warmed to 50° C. To the above mixture was added hydroxylamine hydrochloride (13.0 g, 180 mmol) in H2O (60 mL), and the mixture was refluxed for 50 mins. After cooling down to room temperature, the insoluble solids was filtered, was washed with excess H2O, and dried in vacuo to provide 12.8 g (89%) of the title compound as a pale yellow solid:

Workup

  1. temperaturewas heated
  2. temperaturethe mixture was refluxed for 50 mins
  3. temperatureAfter cooling down to room temperature
  4. filtrationthe insoluble solids was filtered
  5. washwas washed with excess H2O
  6. customdried in vacuo

Sources & evidence

ORD record
ord-3122f1f66fb5480c920cee7f7d06541a
Source dataset
uspto-grants-1999_11
Patent number
US05990126

Reaction notes

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