1,4-Dioxane → 3(2H)-Pyridazinone, 5-(((3-butoxy-4-methoxyphenyl)methyl)amino)-4-chloro-6-ethoxy-

HRID 1111140Notes

Reaction equation

HRID 1111140 reaction equation
[Cl:1][C:2]1[C:3](=[O:12])[NH:4][N:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1Cl.[CH2:13]([O:17][C:18]1[CH:19]=[C:20]([CH:23]=[CH:24][C:25]=1[O:26][CH3:27])[CH2:21][NH2:22])[CH2:14][CH2:15][CH3:16].O1CCOCC1>O>[Cl:1][C:2]1[C:3](=[O:12])[NH:4][N:5]=[C:6]([O:9][CH2:10][CH3:11])[C:7]=1[NH:22][CH2:21][C:20]1[CH:23]=[CH:24][C:25]([O:26][CH3:27])=[C:18]([O:17][CH2:13][CH2:14][CH2:15][CH3:16])[CH:19]=1

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 15079010HCID 15079010, compoundHCID 15079026HCID 15079026, compound

Product 1

HCID 30883383(2H)-Pyridazinone, 5-(((3-butoxy-4-methoxyphenyl)methyl)amino)-4-chloro-6-ethoxy-

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture comprising 7.32 g of 4,5-dichIoro-6-ethoxy-3(2H)pyridazinone prepared in Reference Example 2, 21.95 g of 3-n-butoxy-4-methoxybenzylamine, 60 ml of 1,4-dioxane and 60 ml of water, was refluxed under stirring for 15 hours. Then, most 1,4-dioxane was distilled off under reduced pressure, and dilute hydrochloric acid was added for acidification. Then, chloroform was added thereto, and the mixture was vigorously shaked. The precipitated crystals were separated by filtration, and the chloroform layer of the filtrate was subjected to liquid separation and washed with water and dried over sodium sulfate. Then, the solvent was distilled off to obtain a light yellow oily substance. The product was crystallized from n-propanol-di-i-propyl ether (1:9 v/v), to obtain 10.48 g of the above identified compound having a melting point of from 117° to 118° C. as colorless crystals.

Workup

  1. temperaturewas refluxed
  2. distillationThen, most 1,4-dioxane was distilled off under reduced pressure, and dilute hydrochloric acid
  3. additionwas added for acidification
  4. additionThen, chloroform was added
  5. customThe precipitated crystals were separated by filtration
  6. customthe chloroform layer of the filtrate was subjected to liquid separation
  7. washwashed with water
  8. dry with materialdried over sodium sulfate
  9. distillationThen, the solvent was distilled off
  10. customto obtain a light yellow oily substance
  11. customThe product was crystallized from n-propanol-di-i-propyl ether (1:9 v/v)
  12. customto obtain 10.48 g of the
  13. customof from 117° to 118° C.

Sources & evidence

ORD record
ord-68568c0257eb492b912204737a62b687
Source dataset
uspto-grants-1990_12
Patent number
US04978665

Reaction notes

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