Water → 2Ethyl-4-bromo-5-(2-furanylmethylamino)-3(2H)pyridazinone

HRID 1085792Notes

Reaction equation

HRID 1085792 reaction equation
[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Br:10])=[C:6](Br)[CH:5]=[N:4]1)[CH3:2].[O:12]1[CH:16]=[CH:15][CH:14]=[C:13]1[CH2:17][NH2:18].C(=O)([O-])[O-].[Na+].[Na+].O>O1CCOCC1>[CH2:1]([N:3]1[C:8](=[O:9])[C:7]([Br:10])=[C:6]([NH:18][CH2:17][C:13]2[O:12][CH:16]=[CH:15][CH:14]=2)[CH:5]=[N:4]1)[CH3:2]

Participants

6

Reactant 4

HCID 962WaterHCID 3438FurfurylamineHCID 10340Sodium CarbonateHCID 106605064,5-Dibromo-2-ethylpyridazin-3(2H)-one

Product 1

HCID 150071872Ethyl-4-bromo-5-(2-furanylmethylamino)-3(2H)pyridazinone

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

A mixture comprising 564 mg of 2-ethyl-4,5-dibromo-3(2H)pyridazinone, 291 mg of 2-furanylmethylamine, 530 mg of sodium carbonate, 15 ml of water and 15 ml of 1,4-dioxane, was refluxed under stirring for 5 hours. The solvent was distilled off under reduced pressure, and water was poured to the residue thus obtained. The mixture was extracted with ethyl acetate. The extract was washed with water and dried over sodium sulfate. Then, the solvent was distilled off. The residue oily substance thus obtained was purified by silica gel column chromatography by using a mixture of benzene/ethyl acetate (volume ratio of 2/1) as developer to obtain 294 mg of the above identified compound as colorless crystals having a melting point of from 120° to 123° C. (as recrystallized from a mixture of ethyl acetate/ethyl ether/n-hexane).

Workup

  1. temperaturewas refluxed
  2. distillationThe solvent was distilled off under reduced pressure, and water
  3. additionwas poured to the residue
  4. customthus obtained
  5. extractionThe mixture was extracted with ethyl acetate
  6. washThe extract was washed with water
  7. dry with materialdried over sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customThe residue oily substance thus obtained
  10. customwas purified by silica gel column chromatography
  11. additiona mixture of benzene/ethyl acetate (volume ratio of 2/1) as developer
  12. customto obtain 294 mg of the
  13. customof from 120° to 123° C.
  14. customas recrystallized from a mixture of ethyl acetate/ethyl ether/n-hexane)

Sources & evidence

ORD record
ord-39b5ca24ec97403ca5e344cb2e014d2a
Source dataset
uspto-grants-1991_04
Patent number
US05011839

Reaction notes

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