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Hydroxyamine hydrochloride → 2,5-Dichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23819
Notes
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Reaction equation

HRID 23819 reaction equation
[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH:8]=O)=[O:5].Cl.[NH2:16][OH:17].[C:18]([O-:21])(=O)C.[Na+]>CO>[Cl:1][C:2]1[CH:13]=[CH:12][C:11]([Cl:14])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:16]([CH:18]=[O:21])[OH:17])=[O:5]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 225906072,5-dichloro-N-(2-oxo-ethyl)-benzamide

Product 1

HCID 225906122,5-Dichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamideYield 166.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,5-dichloro-N-(2-oxo-ethyl)-benzamide (0.67 g, 2.9 mmol) in MeOH (100 mL) was added hydroxylamine hydrochloride (0.41 g, 5.8 mmol) and sodium acetate (0.48 g, 5.8 mmol). The mixture was stirred 18 h and the MeOH was removed in vacuo. The residue was dried in vacuo for 18 h and used without further purification to provide the title compound (1.34 g) as a white solid. ESMS: M+H=247.

Workup

  1. customthe MeOH was removed in vacuo
  2. customThe residue was dried in vacuo for 18 h
  3. customused without further purification

Sources & evidence

ORD record
ord-c118b164c23047279ae3bf0e65a4936f
Source dataset
uspto-grants-2005_02
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US06852882B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes