Ethylene Glycol → HCID 18412020, compound

HRID 992264Notes

Reaction equation

HRID 992264 reaction equation
[C:1]([C:4]1[C:5]([CH3:19])=[C:6]([Br:18])[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=1)(=[O:3])[CH3:2].[CH2:20](O)[CH2:21][OH:22].C1(C)C=CC(S(O)(=O)=O)=CC=1.O>C1(C)C=CC=CC=1>[Br:18][C:6]1[C:7](=[O:17])[N:8]([C:10]2[CH:15]=[CH:14][C:13]([F:16])=[CH:12][CH:11]=2)[N:9]=[C:4]([C:1]2([CH3:2])[O:22][CH2:21][CH2:20][O:3]2)[C:5]=1[CH3:19]

Participants

6

Reactant 4

HCID 174Ethylene GlycolHCID 962WaterHCID 6101p-Toluenesulfonic acidHCID 18412002HCID 18412002, compound

Product 1

HCID 18412020HCID 18412020, compoundYield 89.4%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Procedure

A suspension of 6-acetyl-4-bromo-2-(4-fluorophenyl)-5-methyl-3(2H)-pyridazinone (3.2 g), ethylene glycol (3.1 g) and p-toluenesulfonic acid (0.2 g) in toluene (35 ml) was heated under reflux for 10 hours with removing water formed. After cooling on standing, the reaction mixture was extracted with ethyl acetate. After washing with a saturated aqueous sodium hydrogen carbonate solution and a brine, the organic layer was dried over anhydrous magnesium sulfate. The solvent was removed by evaporation, the resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2), and the resulting crude crystals were washed with hexane to obtain 4-bromo-2-(4-fluorophenyl)-5-methyl-6-(2-methyl-1,3-dioxolan-2-yl)-3(2H)-pyridazinone (3.25 g).

Workup

  1. temperaturewas heated
  2. customformed
  3. temperatureAfter cooling
  4. extractionthe reaction mixture was extracted with ethyl acetate
  5. washAfter washing with a saturated aqueous sodium hydrogen carbonate solution
  6. dry with materiala brine, the organic layer was dried over anhydrous magnesium sulfate
  7. customThe solvent was removed by evaporation
  8. customthe resulting residue was purified by silica gel column chromatography (ethyl acetate:hexane=1:2)
  9. washthe resulting crude crystals were washed with hexane

Sources & evidence

ORD record
ord-3dde0a3dc2364b2cbdf014e8df4d5f00
Source dataset
uspto-grants-2002_10
Patent number
US06469003B1

Reaction notes

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