Hydroxylamine HCl → N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine

HRID 1636018

Reaction equation

HRID 1636018 reaction equation
[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=O.[Cl-].[OH:16][NH3+:17].C([O-])(=O)C.[Na+]>C(O)C.O>[F:1][C:2]([F:14])([F:13])[C:3]([C:5]1[CH:10]=[CH:9][C:8]([O:11][CH3:12])=[CH:7][CH:6]=1)=[N:17][OH:16]

Participants

6

Reactant 3

HCID 21645Hydroxylamine HClHCID 1365552,2,2-Trifluoro-4'-methoxyacetophenoneHCID 517045Sodium Acetate

Product 1

HCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamineYield 75.2%

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 962WaterSolvent

Procedure

37.2 g (0.182 mol) of 2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone are dissolved in 150 ml of ethanol at 80° C. To the solution are added dropwise 13.3 g (0.191 mol) of hydroxylammonium chloride and 25.4 g (0.309 mol) of sodium acetate dissolved in 75 ml of water. The reaction mixture is refluxed for 4 hours. The mixture is poured into ice water, the precipitate is filtered, yielding 30.0 g of 2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone oxime as a pale yellow solid. The crude product is used in the next reaction step without further purification.

Workup

  1. temperatureThe reaction mixture is refluxed for 4 hours
  2. filtrationthe precipitate is filtered

Sources & evidence

ORD record
ord-c343d797b2224c5d9241bcd66e878435
Source dataset
uspto-grants-2003_01
Patent number
US06512020B1

Linked notes

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