Sodium hydrosulfide → 4-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinone

HRID 2352515Notes

Reaction equation

HRID 2352515 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8](Cl)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[SH-:14].[Na+]>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([SH:14])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

4

Reactant 2

HCID 28015Sodium hydrosulfideHCID 27822252-Tert-butyl-4,5-dichloro-2,3-dihydropyridazin-3-one

Product 1

HCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinoneYield 81.5%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
60 °C

Procedure

To 560 ml of water were added 66.3 g of 2-tert.-butyl-4,5-dichloro-3(2H)-pyridazinone and 48.0 g of 70% sodium hydrosulfide. After stirring at 60° C. for 4 hours activated carbon was added thereto. The resulting mixture was allowed to cool and then filtered. Concentrated hydrochloric acid was added to the resuling filtrate until the pH thereof was lowered to 2 or less. The resulting solid was filtered off, washed with water, dried and then recrystallized from a mixed solvent of benene and n-hexane to give the intended product as white needle-like crystals of m.p. 112°-113° C. (yield: 81.5%).

Workup

  1. additionwas added
  2. temperatureto cool
  3. filtrationfiltered
  4. additionConcentrated hydrochloric acid was added to the resuling filtrate until the pH
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallized from a mixed solvent of benene and n-hexane

Sources & evidence

ORD record
ord-335ca8ae232c4ab098c5d50d58bf1848
Source dataset
uspto-grants-1989_10
Patent number
US04877787

Reaction notes

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