Ethanol → HCID 86754293, compound

HRID 583108Notes

Reaction equation

HRID 583108 reaction equation
[CH3:1][N:2]1[CH2:7][CH2:6][N:5]([C:8]2[CH:9]=[C:10]([CH:17]=[CH:18][C:19]=2[O:20][CH3:21])[CH2:11][NH:12][O:13][CH:14]=[C:15]=[O:16])[CH2:4][CH2:3]1.[Cl:22][C:23]1[C:24](=[O:30])[NH:25][N:26]=[CH:27][C:28]=1Cl.C(N(CC)CC)C.C(O)C>O>[Cl:22][C:23]1[C:24](=[O:30])[NH:25][N:26]=[CH:27][C:28]=1[N:12]([O:13][CH:14]=[C:15]=[O:16])[CH2:11][C:10]1[CH:17]=[CH:18][C:19]([O:20][CH3:21])=[C:8]([N:5]2[CH2:6][CH2:7][N:2]([CH3:1])[CH2:3][CH2:4]2)[CH:9]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 8471TriethylamineHCID 732474,5-Dichloro-3-hydroxypyridazineHCID 867542923-(4-Methylpiperazin-1-yl)-carbonylmethoxy-4-methoxybenzylamine

Product 1

HCID 86754293HCID 86754293, compoundYield 47.9%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 1.16 g of 3-(4-methylpiperazin-1-yl)-carbonylmethoxy-4-methoxybenzylamine, 0.5 g of 4,5-dichloro-3(2H)-pyridazinone, 0.46 g of triethylamine, 10 ml of ethanol and 10 ml of water, was refluxed under heating with stirring overnight. The solvent was distilled off under reduced pressure, and an aqueous potassium carbonate solution was added to the residue. The mixture was extracted with chloroform. The extract solution was washed with water and a saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate. Then, the solvent was distilled off. The obtained residue was purified by silica gel column chromatography and then crystallized from chloroform/diethyl ether to obtain 0.61 g of the above-identified compound as white crystals.

Workup

  1. temperaturewas refluxed
  2. temperatureunder heating
  3. distillationThe solvent was distilled off under reduced pressure
  4. additionan aqueous potassium carbonate solution was added to the residue
  5. extractionThe mixture was extracted with chloroform
  6. washThe extract solution was washed with water
  7. dry with materiala saturated sodium chloride aqueous solution and then dried over anhydrous sodium sulfate
  8. distillationThen, the solvent was distilled off
  9. customThe obtained residue was purified by silica gel column chromatography
  10. customcrystallized from chloroform/diethyl ether

Sources & evidence

ORD record
ord-9eee5d55776a4bcfbc8c29cfab6e60d5
Source dataset
uspto-grants-1999_07
Patent number
US05929074

Reaction notes

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