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

HRID 470218노트

반응식

HRID 470218 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-a991bc4678824ac2b38ecdac8221847b
출처 데이터셋
uspto-grants-2014_01
특허 번호
US08629270B2

반응 노트

불러오는 중…