Pyridine → 6-amino-2-methylpyridazine-3(2H)-thione

HRID 862480Notes

Reaction equation

HRID 862480 reaction equation
N1C=CC=CC=1.COC1C=CC(P2(SP(C3C=CC(OC)=CC=3)(=S)S2)=[S:16])=CC=1.[NH2:29][C:30]1[CH:35]=[CH:34][C:33](=O)[N:32]([CH3:37])[N:31]=1.C(Cl)(Cl)Cl>CO>[NH2:29][C:30]1[CH:35]=[CH:34][C:33](=[S:16])[N:32]([CH3:37])[N:31]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 6212ChloroformHCID 87949Lawesson's reagentHCID 157119126-Amino-2-methyl-2,3-dihydropyridazin-3-one

Product 1

HCID 196983986-amino-2-methylpyridazine-3(2H)-thioneYield 64.3%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Pyridine (5 ml) and a Lawesson's reagent (970 mg, 2.4 mmol) were added to 3-amino-1-methyl-1,6-dihydropyridazin-6-one (500 mg, 4 mmol) as described in Journal of Medicinal Chemistry, 34 (10), 3074 (1991), and the mixture was refluxed under heating for 5 hours. The reaction mixture was concentrated and the residue obtained was subjected to silica gel column chromatography (chloroform:methanol=100:1) to give 218 mg of 3-amino-1-methyl-1,6-dihydropyridazine-6-thione.

Workup

  1. temperaturethe mixture was refluxed
  2. temperatureunder heating for 5 hours
  3. concentrationThe reaction mixture was concentrated
  4. customthe residue obtained

Sources & evidence

ORD record
ord-8669ca35e835445da07adb346df577bd
Source dataset
uspto-grants-1998_02
Patent number
US05719155

Reaction notes

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