Hydrochloric Acid → N-(4-Bromo-2-ethyl-phenyl)-2-hydroxyimino-acetamide

HRID 2249527Notes

Reaction equation

HRID 2249527 reaction equation
[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH2:9][CH3:10])[CH:3]=1.Cl.S([O-])([O-])(=O)=O.[Na+].[Na+].Cl.[NH2:20][OH:21].Cl[C:23](Cl)(Cl)[CH:24]([OH:26])O>O>[Br:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:24](=[O:26])[CH:23]=[N:20][OH:21])=[C:4]([CH2:9][CH3:10])[CH:3]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochlorideHCID 28012834-Bromo-2-ethylaniline

Product 1

HCID 86041545N-(4-Bromo-2-ethyl-phenyl)-2-hydroxyimino-acetamideYield 46%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a suspension of 4-bromo-2-ethylaniline (50.0 g, 250 mmol) in water (1000 mL) was added concentrated hydrochloric acid (25 mL), sodium sulfate (220 g), and hydroxylamine hydrochloride (56.25 g), followed by addition of chloral hydrate (44.0 g). The reaction mixture was heated to 90° C. using an oil bath for 1 hour. After cooling down to room temperature, it was extracted with ethyl acetate. Extract was dried over magnesium sulfate and concentrated under reduced pressure to give the title compound (31.1 g, 46% yield). 1H NMR (DMSO-d6) δ 12.24 (s, 1H), 9.56 (s, 1H), 7.68 (s, 1H), 7.41 (m, 3H), 2.58 (q, 2H), 1.11 (t, 3H).

Workup

  1. customfor 1 hour
  2. temperatureAfter cooling down to room temperature
  3. extractionit was extracted with ethyl acetate
  4. extractionExtract
  5. dry with materialwas dried over magnesium sulfate
  6. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-6b5adf11534f4234bc70f331248c1f8f
Source dataset
uspto-grants-2008_01
Patent number
US07314886B2

Reaction notes

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