2-Methylimidazole → 4-chloro-2-methyl-5-(2-methyl-imidazol-1-yl)-2H-pyridazin-3-one

HRID 2194413Notes

Reaction equation

HRID 2194413 reaction equation
[Cl:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1Cl.[CH3:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1>O1CCOCC1>[Cl:1][C:2]1[C:3](=[O:10])[N:4]([CH3:9])[N:5]=[CH:6][C:7]=1[N:13]1[CH:14]=[CH:15][N:16]=[C:12]1[CH3:11]

Participants

4

Reactant 2

HCID 127492-MethylimidazoleHCID 1204623(2H)-Pyridazinone, 4,5-dichloro-2-methyl-

Product 1

HCID 668649334-chloro-2-methyl-5-(2-methyl-imidazol-1-yl)-2H-pyridazin-3-oneYield 27.3%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A solution of 10.0 g (54.2 mmol) of 4,5-Dichloro-2-methyl-2H-pyridazin-3-one (CAS: [933-76-6]) and 8.90 g (108.4 mmol) of 2-methylimidazole in 50 ml of dioxane was stirred for 16 h at 100° C. The solution was concentrated in vaccuo and the residue was purified by flash chromatography over silicagel using a 95:5 mixture of methylene chloride and methanol as eluant to yield 3.33 g (14.82 mmol, 27%) of the title compound as a white crystalline solid, MS: m/e=225.1, 227.1 (M+H+).

Workup

  1. concentrationThe solution was concentrated in vaccuo
  2. customthe residue was purified by flash chromatography over silicagel
  3. additiona 95:5 mixture of methylene chloride and methanol as eluant

Sources & evidence

ORD record
ord-3d5073b0700e45c4bb21f79808064ccb
Source dataset
uspto-grants-2012_12
Patent number
US08334287B2

Reaction notes

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