Hydrochloric Acid → N-(4-Ethylphenyl)-2-(hydroxyimino)acetamide

HRID 1725863Notes

Reaction equation

HRID 1725863 reaction equation
Cl[C:2](Cl)(Cl)[CH:3]([OH:5])O.S([O-])([O-])(=O)=O.[Na+].[Na+].[CH2:15]([C:17]1[CH:23]=[CH:22][C:20]([NH2:21])=[CH:19][CH:18]=1)[CH3:16].Cl.Cl.[NH2:26][OH:27]>O>[CH2:15]([C:17]1[CH:23]=[CH:22][C:20]([NH:21][C:3](=[O:5])[CH:2]=[N:26][OH:27])=[CH:19][CH:18]=1)[CH3:16]

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 115044-EthylanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6708876N-(4-Ethylphenyl)-2-(hydroxyimino)acetamide

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Conditions

Temperature
80 °C

Procedure

A mixture of chloral hydrate (26.48 g, 160 mmol), anhydrous sodium sulfate (381 g, 2.68 mol), and 4-ethylaniline (18.6 mL, 150 mmol) in water (910 mL) at 80° C. was treated sequentially with concentrated HCl (20 mL) and a solution of hydroxylamine hydrochloride (31.8 g, 458 mmol) in water (150 mL). The mixture was heated to 80° C. for 1 hour, cooled to room temperature, and filtered. The filter cake was dried under vacuum to provide the desired product. MS (DCI) m/e 193 (M+H)+, 211 (M+NH4)+.

Workup

  1. temperaturecooled to room temperature
  2. filtrationfiltered
  3. customThe filter cake was dried under vacuum

Sources & evidence

ORD record
ord-49fe33637024450f87b73b42e5e5344c
Source dataset
uspto-grants-2009_02
Patent number
US07491718B2

Reaction notes

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