Water → 2-tert.-butyl-4-methyl-5-methylthio-3(2H)-pyridazinone

HRID 2352014Notes

Reaction equation

HRID 2352014 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([SH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].CI.[C:16](=O)([O-])[O-].[Na+].[Na+].O>CN(C)C=O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([S:13][CH3:16])[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 6328Methyl iodideHCID 10340Sodium CarbonateHCID 138222652-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone

Product 1

HCID 138251612-tert.-butyl-4-methyl-5-methylthio-3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The crude product 2.0 g (0.01 mol) of 2-tert.-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone as synthesized in the above and 1.4 g (0.01 mol) of methyl iodide were dissolved in 20 ml of dimethylformamide and then added with 2.0 g of sodium carbonate with stirring at room temperature. The reaction liquid was stirred for 3 hours at 70° C. After allowing to cool the reaction liquid was poured into 200 ml of water and extracted with 50 ml of benzene. The benzene layer was washed successively with 50 ml of 10% sodium hydroxide, 50 ml of 1N hydrochloric acid and 100 ml of water, dried over anhydrous sodium sulfate and freed of solvent by distillation to give 2.0 g of a crude product. The crude product was recrystallized from 20 ml of isopropyl ether to give 1.4 g of 2-tert.-butyl-4-methyl-5-methylthio-3(2H)-pyridazinone.

Workup

  1. customThe reaction liquid
  2. stirringwas stirred for 3 hours at 70° C
  3. temperatureto cool
  4. customthe reaction liquid
  5. extractionextracted with 50 ml of benzene
  6. washThe benzene layer was washed successively with 50 ml of 10% sodium hydroxide, 50 ml of 1N hydrochloric acid and 100 ml of water
  7. dry with materialdried over anhydrous sodium sulfate
  8. distillationfreed of solvent by distillation
  9. customto give 2.0 g of a crude product
  10. customThe crude product was recrystallized from 20 ml of isopropyl ether

Sources & evidence

ORD record
ord-7353e3e4b4534911a5dccdc5e40a4a37
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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