Pyridine → N-[2-(5-Fluorothiophen-2-yl)-2-(hydroxyimino)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine

HRID 1618994ノート

反応式

HRID 1618994 の反応式
[CH2:1]([N:4]([CH2:14][CH:15]=[CH2:16])[CH2:5][C:6]([C:8]1[S:9][C:10]([F:13])=[CH:11][CH:12]=1)=O)[CH:2]=[CH2:3].N1C=CC=CC=1.Cl.[NH2:24][OH:25]>C(O)C>[F:13][C:10]1[S:9][C:8]([C:6](=[N:24][OH:25])[CH2:5][N:4]([CH2:14][CH:15]=[CH2:16])[CH2:1][CH:2]=[CH2:3])=[CH:12][CH:11]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 443297Hydroxyamine hydrochlorideHCID 866978892-(Diallylamino)-1-(5-fluoro-2-thienyl)ethanone

生成物 1

HCID 86697904N-[2-(5-Fluorothiophen-2-yl)-2-(hydroxyimino)ethyl]-N-(prop-2-en-1-yl)prop-2-en-1-amine収率 99%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
70 °C

実験手順

To a stirred solution of 2-(diallylamino)-1-(5-fluoro-2-thienyl)ethanone (4.051 g, 16.93 mmol) in ethanol (34 mL) under nitrogen is added pyridine (4.8 mL, 59.2 mmol) and hydroxylamine hydrochloride (2.94 g, 42.3 mmol). The mixture is heated to 70° C. for 4 hours. The mixture is allowed to cool and then concentrated under reduced pressure. The residue is diluted with ethyl acetate (100 mL) and water (50 mL). The phases are separated and the aqueous phase extracted with ethyl acetate (50 mL). The combined organic extracts are dried over sodium sulfate, filtered, and concentrated to give the title compound (4.25 g, 99%) (approximately a 1.4:1 mixture of oxime isomers by 1H-NMR (CDCl3). ES/MS (m/e): 255 (M+H).

後処理

  1. temperatureto cool
  2. concentrationconcentrated under reduced pressure
  3. additionThe residue is diluted with ethyl acetate (100 mL) and water (50 mL)
  4. customThe phases are separated
  5. extractionthe aqueous phase extracted with ethyl acetate (50 mL)
  6. dry with materialThe combined organic extracts are dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated

出典と根拠

ORDレコード
ord-3da78ef5f180476bb3ab235a6626a82a
出典データセット
uspto-grants-2014_07
特許番号
US08772282B2

反応ノート

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