Water → 2-t-butyl-4-chloro-5-[4-(2-ethoxyethoxy)benzyloxy]-3(2H)-pyridazinone

HRID 1904234Notes

Reaction equation

HRID 1904234 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([OH:13])[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:14]([O:16][CH2:17][CH2:18][O:19][C:20]1[CH:27]=[CH:26][C:23]([CH2:24]Br)=[CH:22][CH:21]=1)[CH3:15].C(=O)([O-])[O-].[K+].[K+].O>CN(C)C=O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:24][C:23]2[CH:22]=[CH:21][C:20]([O:19][CH2:18][CH2:17][O:16][CH2:14][CH3:15])=[CH:27][CH:26]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 146717934-(2-Ethoxyethoxy)-benzyl bromideHCID 546869462-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 146717942-t-butyl-4-chloro-5-[4-(2-ethoxyethoxy)benzyloxy]-3(2H)-pyridazinoneYield 58.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

In 10 ml of N,N-dimethylformamide were dissolved 1.0 g of 2-t-butyl-4-chloro-5-hydroxy-3(2H)-pyridazinone and 1.3 g of 4-(2-ethoxyethoxy)-benzyl bromide, and then 1.0 g of anhydrous potassium carbonate was added thereto. The mixture was heated with stirring on an oil bath at 90° to 100° C. for 3 hours, poured into water, extracted with benzene, washed with water and dried over anhydrous sodium sulfate. Benzene was distilled off under reduced pressure and the resulting oil was purified by means of column chromatography (on silica gel, eluting with benzene/ethyl acetate=18/1) and recrystallization (from n-hexane-benzene) to obtain 1.1 g of the aimed compound, m.p. 82.0°~83.0° C.

Workup

  1. temperatureThe mixture was heated
  2. extractionextracted with benzene
  3. washwashed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationBenzene was distilled off under reduced pressure
  6. customthe resulting oil was purified by means of column chromatography (on silica gel, eluting with benzene/ethyl acetate=18/1) and recrystallization (from n-hexane-benzene)

Sources & evidence

ORD record
ord-4aa05d62b5d942c1a6e66b3c792940ce
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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