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

HRID 338091노트

반응식

HRID 338091 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

반응 조건

온도
70 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7dd9cc8f6cf04af78dddb166c14366c6
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08889856B2

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