p-Chlorothiophenol → HCID 18412010, compound

HRID 992261Notes

Reaction equation

HRID 992261 reaction equation
[OH-].[Na+].[Cl:3][C:4]1[CH:9]=[CH:8][C:7]([SH:10])=[CH:6][CH:5]=1.[C:11]([C:14]1[C:15]([CH3:29])=[C:16](Br)[C:17](=[O:27])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:19]=1)(=[O:13])[CH3:12]>O.CN(C)C=O>[C:11]([C:14]1[C:15]([CH3:29])=[C:16]([S:10][C:7]2[CH:8]=[CH:9][C:4]([Cl:3])=[CH:5][CH:6]=2)[C:17](=[O:27])[N:18]([C:20]2[CH:25]=[CH:24][C:23]([Cl:26])=[CH:22][CH:21]=2)[N:19]=1)(=[O:13])[CH3:12]

Participants

6

Reactant 3

HCID 7815p-ChlorothiophenolHCID 14798Sodium HydroxideHCID 18412017HCID 18412017, compound

Product 1

HCID 18412010HCID 18412010, compoundYield 73%

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 6228DimethylformamideSolvent

Procedure

To a solution of 97% sodium hydroxide (51 mg) in a mixture of water (3 ml) and N,N-dimethylformamide (10 ml) was added 4-chlorothiophenol (0.19 g), followed by stirring at room temperature for 30 minutes. Then, 6-acetyl-4-bromo-2-(4-chlorophenyl)-5-methyl-3(2H)-pyridazinone (0.30 g) was added, followed by stirring at room temperature for 1 hour. Water was added to the reaction mixture and the mixture was extracted with ethyl acetate. After washing with water and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, the resulting crude crystals were recrystallized from ethyl acetate/hexane to obtain 6-acetyl-2-(4-chlorophenyl)-4-(4-chlorophenylthio)-5-methyl-3(2H)-pyridazinone (260 mg) (Compound No. 1-29).

Workup

  1. stirringby stirring at room temperature for 1 hour
  2. extractionthe mixture was extracted with ethyl acetate
  3. washAfter washing with water
  4. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  5. customThe solvent was removed by evaporation
  6. customthe resulting crude crystals were recrystallized from ethyl acetate/hexane

Sources & evidence

ORD record
ord-724bb96ae88e4a61bc2d602a2afdee24
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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