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

HRID 1494518Notes

Reaction equation

HRID 1494518 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 resulting 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 benzene 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 resulting filtrate until the pH
  5. filtrationThe resulting solid was filtered off
  6. washwashed with water
  7. customdried
  8. customrecrystallized from a mixed solvent of benzene and n-hexane

Sources & evidence

ORD record
ord-13f28d627a2c4f0cb03bca159068934d
Source dataset
uspto-grants-1991_06
Patent number
US05026850

Reaction notes

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