Water → 4-bromo-2-ethyl-5-(4-methoxymethoxybenzyloxy)-3(2H)-pyridazinone

HRID 1904236Notes

Reaction equation

HRID 1904236 reaction equation
[Br:1][C:2]1[C:3](=[O:11])[N:4]([CH2:9][CH3:10])[N:5]=[CH:6][C:7]=1Br.[CH3:12][O:13][CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([CH2:20][OH:21])=[CH:18][CH:17]=1.[OH-].[K+].O>CN(C)C=O>[Br:1][C:2]1[C:3](=[O:11])[N:4]([CH2:9][CH3:10])[N:5]=[CH:6][C:7]=1[O:21][CH2:20][C:19]1[CH:18]=[CH:17][C:16]([O:15][CH2:14][O:13][CH3:12])=[CH:23][CH:22]=1

Participants

6

Reactant 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 106605064,5-Dibromo-2-ethylpyridazin-3(2H)-oneHCID 116079844-Methoxymethoxybenzylalcohol

Product 1

HCID 146717974-bromo-2-ethyl-5-(4-methoxymethoxybenzyloxy)-3(2H)-pyridazinoneYield 28.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 30 ml of N,N-dimethylformamide were dissolved 1.2 g of 4,5-dibromo-2-ethyl-3(2H)-pyridazinone and 0.88 g of 4-methoxymethoxybenzyl alcohol, and 0.34 g of powdery potassium hydroxide was added thereto. The reaction mixture was stirred overnight at room temperature, poured into water and extracted with benzene. The benzene layer was washed with water, dried over anhydrous sodium sulfate and freed of the benzene by distillation under reduced pressure. The resulting oil was purified by means of TLC [eluting with benzene/ethyl acetate (12/1)] and recrystallization (from benzene/n-hexane) to obtain 450 mg of the aimed compound, m.p. 104°~106.0° C.

Workup

  1. additionwas added
  2. extractionextracted with benzene
  3. washThe benzene layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationfreed of the benzene by distillation under reduced pressure
  6. customThe resulting oil was purified by means of TLC [eluting with benzene/ethyl acetate (12/1)] and recrystallization (from benzene/n-hexane)

Sources & evidence

ORD record
ord-ce4576a8c8ff4514b0942948f62c4592
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

Loading…