Water → 4-(4-Chlorophenyl)-6-methyl-3-[4(methylthio)phenyl]pyridazine

HRID 432659ノート

反応式

HRID 432659 の反応式
O.[NH2:2][NH2:3].[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([CH:11]([C:16]([C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=O)[CH2:12][C:13](=O)[CH3:14])=[CH:7][CH:6]=1.O>C(O)C>[Cl:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]2[CH:12]=[C:13]([CH3:14])[N:3]=[N:2][C:16]=2[C:18]2[CH:23]=[CH:22][C:21]([S:24][CH3:25])=[CH:20][CH:19]=2)=[CH:7][CH:6]=1

参加物

5

反応物 3

HCID 962WaterHCID 24654Hydrazine hydrate (1:1)HCID 187599824-(4-Chlorophenyl)-5-[4-(methylthio)phenyl]pentane-2,5-dione

生成物 1

HCID 187600234-(4-Chlorophenyl)-6-methyl-3-[4(methylthio)phenyl]pyridazine収率 64.4%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
80 °C

実験手順

Hydrazine hydrate (72 mg, 1.44 mmol) was added to a solution of 4-(4-chlorophenyl)-5-[4-(methylthio)phenyl]pentane-2,5-dione (317 mg, 0.953 mmol) in ethanol (6 ml), and the resulting mixture was stirred for 7 hours at a bath temperature of 80° C. Water was added to the reaction mixture, followed by extraction with ethyl acetate. The extract was washed successively with water and brine, and was then dried over anhydrous sodium sulfate. The solvent was distilled off and the residue (320 mg) was dissolved in chloroform. The thus-obtained solution was stirred at room temperature for 7 hours to conduct air oxidation. The solvent was distilled off and the residue (296 mg) was separated and purified by preparative thin-layer chromatography on silica gel (developing solvent: chloroform), whereby the title compound was obtained as a pale yellow oil (200.5 mg, 64.3%).

後処理

  1. extractionfollowed by extraction with ethyl acetate
  2. washThe extract was washed successively with water and brine
  3. dry with materialwas then dried over anhydrous sodium sulfate
  4. distillationThe solvent was distilled off
  5. dissolutionthe residue (320 mg) was dissolved in chloroform
  6. stirringThe thus-obtained solution was stirred at room temperature for 7 hours
  7. distillationThe solvent was distilled off
  8. customthe residue (296 mg) was separated
  9. custompurified by preparative thin-layer chromatography on silica gel (developing solvent: chloroform), whereby the title compound

出典と根拠

ORDレコード
ord-eb61cbdc23a64c26a4b8c2d9cda7cd7a
出典データセット
uspto-grants-2003_12
特許番号
US06664256B1

反応ノート

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