Ethyl Acetate → 4,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine

HRID 654774노트

반응식

HRID 654774 반응식
Cl.[F:2][C:3]1[CH:8]=[CH:7][C:6]([NH:9][NH2:10])=[CH:5][CH:4]=1.[Na].[CH3:12][S:13][C:14]1[CH:19]=[CH:18][C:17]([CH:20]=[CH:21][C:22]#[N:23])=[CH:16][CH:15]=1.C(OCC)(=O)C>C(O)C.O>[F:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:20]([C:17]3[CH:18]=[CH:19][C:14]([S:13][CH3:12])=[CH:15][CH:16]=3)[CH2:21][C:22]([NH2:23])=[N:10]2)=[CH:5][CH:4]=1

참가 물질

7

반응물 4

HCID 8857Ethyl AcetateHCID 699814-Fluorophenylhydrazine hydrochlorideHCID 42396803-[4-(Methylthio)phenyl]acrylonitrileHCID 5360545Sodium

생성물 1

HCID 104945294,5-Dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine수율 67.6%

시약·촉매·용매 2

HCID 702Ethanol용매HCID 962Water용매

실험 절차

4-Fluorophenylhydrazine hydrochloride 4 g) was added to a solution of sodium (1.13 g) in ethanol (50 ml), and the mixture was refluxed for 1 hour. To the cooled mixture was added 3-[4-(methylthio)phenyl]acrylonitrile (4.3 g), and the resulting mixture was refluxed overnight. Ethyl acetate and water were added, and the organic layer was separated, dried and concentrated. The oily residue (7.6 g) was purified by column chromatography on silica gel (76 g) eluting with a mixture of toluene and ethyl acetate (2:1) to give brown crystals of 4,5-dihydro-1-(4-fluorophenyl)-5-[4-(methylthio)phenyl]pyrazol-3-amine (5 g).

후처리

  1. temperaturethe mixture was refluxed for 1 hour
  2. temperaturethe resulting mixture was refluxed overnight
  3. customthe organic layer was separated
  4. customdried
  5. concentrationconcentrated
  6. customThe oily residue (7.6 g) was purified by column chromatography on silica gel (76 g)
  7. washeluting with a mixture of toluene and ethyl acetate (2:1)

출처 및 근거

ORD 기록
ord-2425888f196f492396fa15bd73dac99d
출처 데이터셋
uspto-grants-1992_07
특허 번호
US05134142

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