Hydroxyamine hydrochloride → 2,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamide

HRID 23816Notes

Reaction equation

HRID 23816 reaction equation
[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH:8]=O)=[O:5].Cl.[NH2:17][OH:18].[C:19]([O-:22])(=O)C.[Na+]>CO>[Cl:1][C:2]1[C:13]([Cl:14])=[CH:12][C:11]([Cl:15])=[CH:10][C:3]=1[C:4]([NH:6][CH2:7][CH2:8][N:17]([CH:19]=[O:22])[OH:18])=[O:5]

Participants

5

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 225905982,3,5-trichloro-N-(2-oxo-ethyl)-benzamide

Product 1

HCID 225905992,3,5-Trichloro-N-[2-(N-formyl-N-hydroxy-amino)-ethyl]-benzamideYield 149.8%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 2,3,5-trichloro-N-(2-oxo-ethyl)-benzamide (0.80 g, 3.0 mmol) in MeOH (100 mL) was added hydroxylamine hydrochloride (0.41 g, 6 mmol) and sodium acetate (0.49 g, 6 mmol). The mixture was stirred 18 h and the MeOH was removed in vacuo. The residue was dried in vacuo for 18 h and was used without further purification to yield the title compound (1.4 g) as a white solid. ESMS: M+H=281.

Workup

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

Sources & evidence

ORD record
ord-8869058050e346d18b30f1429ace0eb4
Source dataset
uspto-grants-2005_02
Patent number
US06852882B2

Reaction notes

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