Pyridine → 4-(1-(1H)-Imidazolyl)-1-phenyl-1-butanone O-(2-aminoethyl)oxime dihydrochloride

HRID 2293086ノート

反応式

HRID 2293086 の反応式
[N:1]1([CH2:6][CH2:7][CH2:8][C:9]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=O)[CH:5]=[CH:4][N:3]=[CH:2]1.[ClH:17].Cl.[NH2:19][CH2:20][CH2:21][O:22][NH2:23].N1C=CC=CC=1>C(O)C>[ClH:17].[ClH:17].[NH2:19][CH2:20][CH2:21][O:22][N:23]=[C:9]([C:11]1[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=1)[CH2:8][CH2:7][CH2:6][N:1]1[CH:5]=[CH:4][N:3]=[CH:2]1

参加物

5

反応物 3

HCID 1049PyridineHCID 130844144-(1-(1H)-imidazolyl)-1-phenyl-1-butanoneHCID 143623262-(O-aminooxy)ethylamine dihydrochloride

生成物 1

HCID 734741694-(1-(1H)-Imidazolyl)-1-phenyl-1-butanone O-(2-aminoethyl)oxime dihydrochloride収率 217.5%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

A mixture of 4-(1-(1H)-imidazolyl)-1-phenyl-1-butanone (3.00 g), O-(2-aminoethyl)hydroxylamine dihydrochloride (2.50 g), 3 equivalents of pyridine, and absolute ethanol (75 ml) was heated under reflux, under nitrogen, with stirring, overnight. The reaction mixture was evaporated, toluene was added and evaporated. The residue was partitioned between 10% sodium hydroxide solution and ethyl acetate. The layers were separated and the aqueous phase extracted with ethyl acetate. The combined organic extracts were dried over anhydrous sodium sulfate, filtered, and the filtrate was evaporated. The residue was combined with 5.0 g of crude, previously prepared material and purified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide). The appropriate fractions were collected and concentrated. The residue was dissolved in absolute ethanol and treated with ethereal hydrogen chloride. Diethyl ether was added. The precipitate was collected and recrystallized from absolute ethanol to give 6.3 g (58%) of product, mp 196°-198° C. (dec).

後処理

  1. temperaturewas heated
  2. temperatureunder reflux, under nitrogen
  3. customThe reaction mixture was evaporated
  4. additiontoluene was added
  5. customevaporated
  6. customThe residue was partitioned between 10% sodium hydroxide solution and ethyl acetate
  7. customThe layers were separated
  8. extractionthe aqueous phase extracted with ethyl acetate
  9. dry with materialThe combined organic extracts were dried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe filtrate was evaporated
  12. custompurified by flash chromatography (180:19:1 dichloromethane/methanol/ammonium hydroxide)
  13. customThe appropriate fractions were collected
  14. concentrationconcentrated
  15. dissolutionThe residue was dissolved in absolute ethanol
  16. additiontreated with ethereal hydrogen chloride
  17. additionDiethyl ether was added
  18. customThe precipitate was collected
  19. customrecrystallized from absolute ethanol

出典と根拠

ORDレコード
ord-c2a0807793444258a00ddbac550fb2b7
出典データセット
uspto-grants-1997_11
特許番号
US05686447

反応ノート

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