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

HRID 654774

反応式

HRID 654774 の反応式
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

参加物

7

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 702Ethanol溶媒HCID 962Water溶媒

実験手順

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).

後処理

  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)

出典と根拠

ORDレコード
ord-2425888f196f492396fa15bd73dac99d
出典データセット
uspto-grants-1992_07
特許番号
US05134142

関連ノート

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