Triethylamine → 1-(4-Tolyl)-3-(4-nitrophenyl)-5-aminopyrazole

HRID 1860515노트

반응식

HRID 1860515 반응식
[C:1]([CH2:3][C:4]([C:6]1[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=1)=O)#[N:2].[C:15]1(C)[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=1[NH:21][NH2:22].[CH2:24](N(CC)CC)C.CCOC(C)=O>C(O)C>[C:19]1([CH3:24])[CH:20]=[CH:15][C:16]([N:21]2[C:1]([NH2:2])=[CH:3][C:4]([C:6]3[CH:11]=[CH:10][C:9]([N+:12]([O-:14])=[O:13])=[CH:8][CH:7]=3)=[N:22]2)=[CH:17][CH:18]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 68256o-TolylhydrazineHCID 5914594-Nitrobenzoylacetonitrile

생성물 1

HCID 120186771-(4-Tolyl)-3-(4-nitrophenyl)-5-aminopyrazole

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

To a solution of 2-cyano-4′nitroacetophenone in ethanol (100 mL) at room temperature was added tolylhydrazine (6.44 g, 0.04 mol) and triethylamine (15.4 mL, 0.11 mol). The resulting solution was heated to reflux and maintained at reflux for 1 h. The solution was cooled to room temperature at which time EtOAc (500 mL) was added. The organic solution was washed with brine (2×500 mL), dried over Na2SO4 and concentrated by rotary evaporation. The residue was purified by column chromatography on silica gel eluting with 1:1 hexane/EtOAc to yield 1-(4-tolyl)-3-(4-nitrophenyl)-5-aminopyrazole as a solid.

후처리

  1. temperatureThe resulting solution was heated
  2. temperatureto reflux
  3. temperaturemaintained
  4. temperatureat reflux for 1 h
  5. additionwas added
  6. washThe organic solution was washed with brine (2×500 mL)
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated by rotary evaporation
  9. customThe residue was purified by column chromatography on silica gel eluting with 1:1 hexane/EtOAc

출처 및 근거

ORD 기록
ord-4da161b0cc6e4e3dbfe5cadb98633822
출처 데이터셋
uspto-grants-2003_03
특허 번호
US06531478B2

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