Sodium hydrosulfide → 2-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinone

HRID 2352013Notes

Reaction equation

HRID 2352013 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8](Cl)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[SH-:14].[Na+]>C(O)C>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH3:12])=[C:8]([SH:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 138222642-tert-butyl-5-chloro-4-methylpyridazin-3-(2H)-one

Product 1

HCID 138222652-t-butyl-5-mercapto-4-methyl-3(2H)-pyridazinoneYield 96.7%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To 75ml of ethanol were added 17.0 g (0.085 mol) of 2-tert.-butyl-5-chloro-4-methyl-3(2H)-pyridazinone and 8.5 g (0.106 mol) of 70% sodium hydrosulfide, and the mixture was stirred under reflux for 4 hours. After cooling, the mixture was poured into 300 ml of ice-water and extracted with 200 ml of ethyl ether. The ether layer was washed with 100 ml of water and dried over anhydrous sodium sulfate. The solvent was then distilled off therefrom to give 16.3 g of a crude product.

Workup

  1. temperatureunder reflux for 4 hours
  2. temperatureAfter cooling
  3. extractionextracted with 200 ml of ethyl ether
  4. washThe ether layer was washed with 100 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationThe solvent was then distilled off

Sources & evidence

ORD record
ord-ea6e550985fa4ef7a3b733fbe95e7ea3
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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