Hydrochloric Acid → Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-

HRID 517434Notes

Reaction equation

HRID 517434 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([CH:6]=[CH:7][CH:8]=1)[NH2:5].Cl[C:10](Cl)(Cl)[CH:11]([OH:13])O.Cl.[NH2:17][OH:18].S([O-])([O-])(=O)=O.[Na+].[Na+].Cl>O>[Br:1][C:2]1[CH:3]=[C:4]([NH:5][C:11](=[O:13])[CH:10]=[N:17][OH:18])[CH:6]=[CH:7][CH:8]=1

Participants

7

Reactant 5

HCID 313Hydrochloric AcidHCID 2707Chloral HydrateHCID 115623-BromoanilineHCID 24436Sodium SulfateHCID 443297Hydroxyamine hydrochloride

Product 1

HCID 6739944Acetamide, N-(3-bromophenyl)-2-(hydroxyimino)-Yield 85%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
90 °C

Procedure

To a 3000 mL round bottom flask, 3-bromoaniline (50 g, 0.2907 mol), water (1500 mL), chloral hydrate (57.7 g, 0.3488 mol), hydroxylamine hydrochloride (64.6 g, 0.9302 mol) and sodium sulfate (250 g) were added. To this reaction mixture conc. HCl (76 mL) was slowly added. The reaction mixture was stirred at 90° C. for 2 h. The white precipitate was formed and was collected by filtration. The white solid was dried to get the title compound [60 g, 85%]. 1H NMR (300 MHz, DMSO-d6): δ 12.28 (s, 1H), 10.38 (s, 1H), 8.03 (t, J=1.5 Hz, 1H), 7.62-7.65 (m, 2H), 7.29-7.31 (m, 2H). LC-MS (ESI): Calculated mass: 242.0; Observed mass: 243.0 [M+H]+ (RT: 0.17 min).

Workup

  1. customThe white precipitate was formed
  2. filtrationwas collected by filtration
  3. customThe white solid was dried

Sources & evidence

ORD record
ord-4a92ca117d614e929b9d4552b704d6cf
Source dataset
uspto-grants-2015_08
Patent number
US09115092B2

Reaction notes

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