Methyl iodide → 6-chloro-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

HRID 2419147Notes

Reaction equation

HRID 2419147 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[N:7]=1.[H-].[Na+].[CH3:14]I>CN(C=O)C.O>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[N:9]([CH3:14])[N:10]=2)[N:7]=1

Participants

6

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 64071826-chloro-2H,3H-[1,2,4]triazolo[4,3-b]pyridazin-3-one

Product 1

HCID 230003286-chloro-2-methyl[1,2,4]triazolo[4,3-b]pyridazin-3(2H)-one

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 6-chloro-2,3-dihydro-s-triazolo[4,3-b]pyridazin-3-one [P. Francavilla and F. Lauria, J. Het. Chem. 8, 415 (1971)] (1, 8.5 g., 50 m.mol.) in dry DMF (12 ml.) was added NaH (50% dispersion in paraffin, 2.64 g., 55 m.mol) and the mixture was stirred for 1 hour at room temperature. After methyl iodide (21.3 g., 150 m.mole) was added, the mixture was stirred for 40 hours at room temperature, diluted with water (200 ml.) and extracted with CHCl3 (4 × 100 ml.). The combined extracts were washed with water (3 × 50 ml.), treated with a small amount of carbon and dried with anhydrous Na2SO4. Evaporation of the solvent under reduced pressure afforded pale yellow residue which was crystallized from chloroform-n-hexane. Yield: 7.23 g. (79%). M.p. 180°-181° C.

Workup

  1. stirringthe mixture was stirred for 40 hours at room temperature
  2. extractionextracted with CHCl3 (4 × 100 ml.)
  3. washThe combined extracts were washed with water (3 × 50 ml.)
  4. additiontreated with a small amount of carbon
  5. dry with materialdried with anhydrous Na2SO4
  6. customEvaporation of the solvent under reduced pressure
  7. customafforded pale yellow residue which
  8. customwas crystallized from chloroform-n-hexane

Sources & evidence

ORD record
ord-ebfeaac9bfdb4c139bc6872b8423126a
Source dataset
uspto-grants-1978_08
Patent number
US04104469

Reaction notes

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