Hydrochloric Acid → Acetamide, 2-(hydroxyimino)-N-phenyl-

HRID 1421494Notes

Reaction equation

HRID 1421494 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].C([C:17]1[CH:18]=[C:19]([CH:21]=[CH:22][CH:23]=1)[NH2:20])C.Cl.Cl.[NH2:26][OH:27]>O>[CH:23]1[CH:22]=[CH:21][C:19]([NH:20][C:3](/[CH:2]=[N:26]/[OH:27])=[O:5])=[CH:18][CH:17]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 114753-EthylanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6861488Acetamide, 2-(hydroxyimino)-N-phenyl-Yield 67.6%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent3×

Conditions

Temperature
50 °C

Procedure

A mixture of chloral hydrate (59.3 g, 0.36 mol), water (700 ml), and sodium sulphate (85.8 g, 0.60 mol), was heated to 50° C. When 50° C. was reached, sequentially a mixture of 3-ethylaniline (40.8 g, 0.33 mol), water (700 ml) and conc. hydrochloric acid (33.6 ml) and a mixture of hydroxylamine hydrocloride (74.8 g, 1.04 mol) and water (330 ml) were added. The resulting mixture was heated to 80° C. during 30 minutes and kept for another 10 minutes at this temperature before the reaction mixture was cooled on an ice-bath. The resulting precipitate was filtered off, washed with water and dried in vacuum over P2O5 to give an isonitrosoacetanilide (36.6 g), yield 58%

Workup

  1. customWhen 50° C.
  2. additionwere added
  3. temperatureThe resulting mixture was heated to 80° C. during 30 minutes
  4. temperaturewas cooled on an ice-bath
  5. filtrationThe resulting precipitate was filtered off
  6. washwashed with water
  7. dry with materialdried in vacuum over P2O5

Sources & evidence

ORD record
ord-0625a89e077843b884d94e3ab804b042
Source dataset
uspto-grants-2000_06
Patent number
US06077851

Reaction notes

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