Water → 3-Chloro-5(methylthio)pyridazine

HRID 743974Notes

Reaction equation

HRID 743974 reaction equation
[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6](Cl)[CH:7]=1.[CH3:9][S-:10].[Na+].O>C1COCC1>[Cl:1][C:2]1[N:3]=[N:4][CH:5]=[C:6]([S:10][CH3:9])[CH:7]=1

Participants

5

Reactant 3

HCID 962WaterHCID 4378561Sodium methanethiolateHCID 199596873,5-Dichloropyridazine

Product 1

HCID 199596713-Chloro-5(methylthio)pyridazineYield 76%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

3,5-Dichloropyridazine, which is known in the art, (2.0 g, 0.0135 moles) and sodium thiomethoxide (1.14 g, 0.0162 moles) were stirred in THF (50 mL) at RT under N2 for 2 h. The mixture was then poured into water and extracted 2×100 mL with ethyl acetate. The organic layer was dried (MgSO4), filtered and evaporated in-vacuo to give a crude solid which was recrystallized from cyclohexane/ethyl acetate to give 3-chloro-5(methylthio)pyridazine (1.64 g, 76% yield) as a brown solid, mp=98° C.-100° C.

Workup

  1. extractionextracted 2×100 mL with ethyl acetate
  2. dry with materialThe organic layer was dried (MgSO4)
  3. filtrationfiltered
  4. customevaporated in-vacuo
  5. customto give a crude solid which
  6. customwas recrystallized from cyclohexane/ethyl acetate

Sources & evidence

ORD record
ord-b52792c0f0b746b9baf46cdaaabc4383
Source dataset
uspto-grants-1996_09
Patent number
US05559080

Reaction notes

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