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

HRID 1904231Notes

Reaction equation

HRID 1904231 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 75 ml of ethanol were added 17.0 g (0.085 mol) of 2-t-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 reflax 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, dried over anhydrous sodium sulfate and then freed of solvent by distillation to obtain 16.3 g of a crude product.

Workup

  1. temperatureAfter cooling
  2. extractionextracted with 200 ml of ethyl ether
  3. washThe ether layer was washed with 100 ml of water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationfreed of solvent by distillation

Sources & evidence

ORD record
ord-a7b87b1a982d44db8a19ec7c8a410a02
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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