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

HRID 1384778

Reaktionsgleichung

Reaktionsgleichung von HRID 1384778
[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]

Komponenten

6

Edukt 3

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

Produkt 1

HCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamineAusbeute 57,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 702EthanolLösungsmittelHCID 962WaterLösungsmittel

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

118.5 g (0.58 mol) of 2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone are dissolved in 470 ml of ethanol and heated at 80° C. To the solution are added 42.4 g (0.61 mol) of hydroxylammonium chloride and 80.9 g (0.99 mol) of sodium acetate dissolved in 240 ml of water. The reaction mixture is refluxed for 5 hours, and the solvent is distilled off by a rotary evaporator. The residue is poured into 500 ml of water, and a white solid is precipitated. The solid is isolated by filtration and rinsed with water, and purified by recrystallization from toluene, yielding 73.1 g of 2,2,2-trifluoro-1-(4-methoxyphenyl)-ethanone oxime as a white solid. The structure is confirmed by the 1H-NMR spectrum (CDCl3). δ[ppm]: 3.84 (s, 3H), 6.99 (d, 2H), 7.55 (d, 2H), 9.11 (br s, 1H). The spectrum indicates the compound is a single isomer, which is tentatively assigned as Z-conformation.

Aufarbeitung

  1. temperatureThe reaction mixture is refluxed for 5 hours
  2. distillationthe solvent is distilled off by a rotary evaporator
  3. additionThe residue is poured into 500 ml of water
  4. customa white solid is precipitated
  5. customThe solid is isolated by filtration
  6. washrinsed with water
  7. custompurified by recrystallization from toluene

Quellen und Nachweise

ORD-Eintrag
ord-80ed111a3aa1451a865ce297542a8356
Quelldatensatz
uspto-grants-2001_07
Patentnummer
US06261738B1

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