Hydrochloric Acid → 3-Chloroacetanilide

HRID 1906567Notes

Reaction equation

HRID 1906567 reaction equation
Cl[C:2](Cl)(Cl)[CH:3](O)[OH:4].S([O-])([O-])(=O)=O.[Na+].[Na+].[Cl:15][C:16]1[CH:17]=[C:18]([CH:20]=[CH:21][CH:22]=1)[NH2:19].Cl.NO>O>[CH3:2][C:3]([NH:19][C:18]1[CH:20]=[CH:21][CH:22]=[C:16]([Cl:15])[CH:17]=1)=[O:4]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 787HydroxylamineHCID 2707Chloral HydrateHCID 79323-ChloroanilineHCID 24436Sodium Sulfate

Product 1

HCID 114933-Chloroacetanilide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent4×

Procedure

To a stirred solution of 113.23 g (0.686 mol) of chloral hydrate in 2 liters of water was added 419 g (2.95 mol) of sodium sulfate, followed by a solution prepared from 89.25 g (0.70 mol) of 3-chloroaniline, 62 ml of concentrated hydrochloric acid and 500 ml of water. A thick precipitate formed. To the reaction mixture was then added, with stirring, a solution of 155 g (2.23 mol) of hydroxylamine in 500 ml of water. Stirring was continued and the reaction mixture was warmed slowly and it was maintained between 60° and 75° C. for approximately 6 hours, during which time an additional 1 liter of water had been added to facilitate stirring. The reaction mixture was then cooled and the precipitate was recovered by filtration. The wet solid was dried to give 136.1 g of isonitroso-3-chloroacetanilide.

Workup

  1. customA thick precipitate formed
  2. additionTo the reaction mixture was then added
  3. stirringStirring
  4. temperaturethe reaction mixture was warmed slowly
  5. additionhad been added
  6. stirringto facilitate stirring
  7. temperatureThe reaction mixture was then cooled
  8. filtrationthe precipitate was recovered by filtration
  9. customThe wet solid was dried

Sources & evidence

ORD record
ord-11195b7bc3e347549db2cab5d307918f
Source dataset
uspto-grants-1987_03
Patent number
US04652658

Reaction notes

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