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

HRID 268648

Reaction equation

HRID 268648 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-1926690a1aa74c89addfd329923aee6a
Source dataset
uspto-grants-2008_11
Patent number
US07446122B2

Linked notes

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