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

HRID 1636022

반응식

HRID 1636022 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

반응 조건

온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-35043ee4f9d6494993b77727ab5a2ac9
출처 데이터셋
uspto-grants-2003_01
특허 번호
US06512020B1

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