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

HRID 432659Notes

Reaction equation

HRID 432659 reaction equation
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

Participants

5

Reactant 3

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

Product 1

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

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
80 °C

Procedure

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%).

Workup

  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

Sources & evidence

ORD record
ord-eb61cbdc23a64c26a4b8c2d9cda7cd7a
Source dataset
uspto-grants-2003_12
Patent number
US06664256B1

Reaction notes

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