Phenylhydrazine → 3-Ethyl-1-phenyl-1H-pyrazol-5-amine

HRID 1918160노트

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HRID 1918160 반응식
O=[C:2]([CH2:6][CH3:7])[CH2:3][C:4]#[N:5].[C:8]1([NH:14][NH2:15])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1>C(O)C>[CH2:6]([C:2]1[CH:3]=[C:4]([NH2:5])[N:14]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[N:15]=1)[CH3:7]

참가 물질

4

반응물 2

HCID 7516PhenylhydrazineHCID 99203693-Oxopentanenitrile

생성물 1

HCID 202977953-Ethyl-1-phenyl-1H-pyrazol-5-amine수율 37.4%

시약·촉매·용매 1

HCID 702Ethanol용매

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온도
90 °C

실험 절차

A stirred mixture of 3-oxopentanenitrile (19.42 g, 0.20 mol) and phenylhydrazine (23.62 g, 0.20 mol) in ethanol (200 mL) was heated at 90° C. for 15 h. The reaction mixture was quenched with water and extracted with dichloromethane. The combined dichloromethane layers were dried over magnesium sulfate, concentrated under reduced pressure, and dried under vacuum to afford the light yellow oil which was purified by silica gel flash column chromatography (eluting with a mixture of 20% ethyl acetate in petroleum ether). The obtained solid was recrystallized from a mixture of 10% petroleum ether in ethyl acetate, to afford 3-ethyl-1-phenyl-1H-pyrazol-5-amine (14 g, 37% over two steps) as a yellow solid. 1H NMR (400 MHz, DMSO-d6) δ 7.57-7.59 (m, 2H), 7.43-7.46 (m, 2H), 7.27 (m, 1H), 5.36 (s, 1H), 5.26 (s, 2H), 2.45 (q, J=7.6 Hz, 2H), 1.15 (t, J=7.6 Hz, 3H); LC-MS (ESI) m/z 188 (M+H)+.

후처리

  1. customThe reaction mixture was quenched with water
  2. extractionextracted with dichloromethane
  3. dry with materialThe combined dichloromethane layers were dried over magnesium sulfate
  4. concentrationconcentrated under reduced pressure
  5. customdried under vacuum
  6. customto afford the light yellow oil which
  7. customwas purified by silica gel flash column chromatography (
  8. washeluting with a mixture of 20% ethyl acetate in petroleum ether)
  9. customThe obtained solid was recrystallized from a mixture of 10% petroleum ether in ethyl acetate

출처 및 근거

ORD 기록
ord-2a3231cc1aa94f2fad12dec31671f79e
출처 데이터셋
uspto-grants-2013_12
특허 번호
US08618289B2

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