Hydroxyamine hydrochloride → 4-[(E)-hydroxyiminomethyl]-3-(trifluoromethyl)-N-(trimethylsilylmethyl)benzamide

HRID 1692572Notes

Reaction equation

HRID 1692572 reaction equation
[CH:1]([C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:8])=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18])=O.Cl.[NH2:22][OH:23].C([O-])(=O)C.[Na+]>CCO.O.C(OC)(C)(C)C>[OH:23]/[N:22]=[CH:1]/[C:3]1[CH:16]=[CH:15][C:6]([C:7]([NH:9][CH2:10][Si:11]([CH3:14])([CH3:13])[CH3:12])=[O:8])=[CH:5][C:4]=1[C:17]([F:20])([F:19])[F:18]

Participants

7

Reactant 3

HCID 443297Hydroxyamine hydrochlorideHCID 517045Sodium AcetateHCID 582709634-formyl-3-(trifluoromethyl)-N-[(trimethylsilyl)methyl]benzamide

Product 1

HCID 582709774-[(E)-hydroxyiminomethyl]-3-(trifluoromethyl)-N-(trimethylsilylmethyl)benzamide

Reagents, catalysts & solvents 3

HCID 702EthanolSolventHCID 962WaterSolventHCID 15413tert-Butyl methyl etherSolvent

Procedure

4-Formyl-3-(trifluoromethyl)-N-[(trimethylsilyl)methyl]benzamide (15.0 g, 49.4 mmol), Hydroxylamine hydrochloride (6.9 g, 98.8 mmol) and sodium acetate (6.1 g, 74.1 mmol) in EtOH and H2O were stirred at room temperature over night. The reaction mixture was diluted with t-BuOMe, and washed with brine and dried over MgSO4. After evaporation the product was found to be 15.0 g (95%).

Workup

  1. washwashed with brine
  2. dry with materialdried over MgSO4
  3. customAfter evaporation the product

Sources & evidence

ORD record
ord-0a4f8dce19584fb0bf11030d3c91fb9e
Source dataset
uspto-grants-2012_04
Patent number
US08158560B2

Reaction notes

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