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

HRID 1636022ノート

反応式

HRID 1636022 の反応式
[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]

参加物

6

反応物 3

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

生成物 1

HCID 59115151N-[2,2,2-Trifluoro-1-(4-methoxyphenyl)ethylidene]hydroxylamine収率 57.5%

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-35043ee4f9d6494993b77727ab5a2ac9
出典データセット
uspto-grants-2003_01
特許番号
US06512020B1

反応ノート

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