Phosphorus oxychloride → 5-Chloro-3-(2-methylimidazol-1-ylmethyl)-pyridazine

HRID 891943Notes

Reaction equation

HRID 891943 reaction equation
[CH3:1][C:2]1[N:3]([CH2:7][C:8]2[NH:13][N:12]=[CH:11][C:10](=O)[CH:9]=2)[CH:4]=[CH:5][N:6]=1.P(Cl)(Cl)([Cl:17])=O>>[Cl:17][C:10]1[CH:9]=[C:8]([CH2:7][N:3]2[CH:4]=[CH:5][N:6]=[C:2]2[CH3:1])[N:13]=[N:12][CH:11]=1

Participants

3

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 22240240HCID 22240240, compound

Product 1

HCID 117890255-Chloro-3-(2-methylimidazol-1-ylmethyl)-pyridazineYield 73%

Conditions

Temperature
60 °C

Procedure

6-(2-Methyl-imidazol-1-ylmethyl)-1H-pyridazin-4-one (3.9 g, 20.5 mmol)) was treated with phosphorus oxychloride (18 ml, 205 mmol) under argon. The mixture was stirred in a 60° C. oilbath for 1.5 hours. The solvent was removed in vacuo and the residue was dissolved in water (100 ml) under icebath cooling. The brown solution was neutralized with solid NaHCO3 and the aqueous layer was extracted with MeCl2 (6×50 ml). The combined extracts were dried over Na2SO4, filtered and the solvent was removed in vacuo to provide 5-chloro-3-(2-methyl-imidazol-1-yl-methyl)-pyridazine (3.1 g, 73%) as a brown solid, MS: m/e=209.3 (M+H+).

Workup

  1. customThe solvent was removed in vacuo
  2. dissolutionthe residue was dissolved in water (100 ml) under icebath
  3. temperaturecooling
  4. extractionthe aqueous layer was extracted with MeCl2 (6×50 ml)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo

Sources & evidence

ORD record
ord-acdce6425db5431e824219834aba9393
Source dataset
uspto-grants-2006_02
Patent number
US07005432B2

Reaction notes

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