Perchloric Acid → O-(2,4-dinitrophenyl)hydroxylamine

HRID 1756494ノート

反応式

HRID 1756494 の反応式
[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:5]=1[O:6][N:7]=C(OCC)C)([O-:3])=[O:2].Cl(O)(=O)(=O)=O>O1CCOCC1>[N+:1]([C:4]1[CH:16]=[C:15]([N+:17]([O-:19])=[O:18])[CH:14]=[CH:13][C:5]=1[O:6][NH2:7])([O-:3])=[O:2]

参加物

4

反応物 2

HCID 24247Perchloric AcidHCID 2724427Ethyl N-(2,4-dinitrophenoxy)ethanimidate

生成物 1

HCID 87140O-(2,4-dinitrophenyl)hydroxylamine収率 190%

試薬・触媒・溶媒 1

HCID 312751,4-Dioxane溶媒

実験手順

To a suspension of 2.0 g (0.0074 mole) of ethyl N-(2,4-dinitrophenoxy)acetimidate in 10 mL of dioxane, cooled in an ice/water bath, was added dropwise 3 mL of 70% perchloric acid during a 10 minute period. The reaction mixture was stirred at 0°-5° C. for five hours and then was poured into 100 mL of ice water. This mixture was extracted three times with 40 mL of methylene chloride. The combined extracts were dried over anhydrous magnesium sulfate and filtered. The solvent was evaporated from the filtrate under reduced pressure, leaving 2.8 g of a brown oil. This oil was dissolved in 20 mL of diethyl ether, and 30 mL of petroleum ether was added to the solution, causing a precipitate to form. This precipitate was recovered by filtration. After being washed with petroleum ether and dried, 0.75 g of O-(2,4-dinitrophenyl)hydroxylamine was recovered as a yellow powder. The NMR spectrum was consistent with the proposed structure. This method is described by Y. Tamura et al., J. Org. Chem., 38, 1239 (1973).

後処理

  1. temperaturecooled in an ice/water bath
  2. extractionThis mixture was extracted three times with 40 mL of methylene chloride
  3. dry with materialThe combined extracts were dried over anhydrous magnesium sulfate
  4. filtrationfiltered
  5. customThe solvent was evaporated from the filtrate under reduced pressure

出典と根拠

ORDレコード
ord-8ada37e1a4cc484b8b5ad3bd24ca0ed0
出典データセット
uspto-grants-1995_08
特許番号
US05441925

反応ノート

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