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Diisopropyl Ether → 2-t-butyl-4-chloro-5-[{6-(4-chlorophenoxy)-3-pyridyl}methyloxy]-3(2H)-pyridazinone

HRID 1904251
Notes
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Reaction equation

HRID 1904251 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].Cl[CH2:15][C:16]1[CH:17]=[CH:18][C:19]([O:22][C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=2)=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)C)(C)C>CC(O)C.O.CN(C)C=O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([O:13][CH2:15][C:16]2[CH:21]=[N:20][C:19]([O:22][C:23]3[CH:28]=[CH:27][C:26]([Cl:29])=[CH:25][CH:24]=3)=[CH:18][CH:17]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 146718265-Chloromethyl-2-(4-chlorophenoxy)-pyridineHCID 546869462-tert-Butyl-4-chloro-5-hydroxypyridazin-3(2H)-one

Product 1

HCID 138223012-t-butyl-4-chloro-5-[{6-(4-chlorophenoxy)-3-pyridyl}methyloxy]-3(2H)-pyridazinoneYield 79.8%

Reagents, catalysts & solvents

3
HCID 962WaterSolventHCID 3776IsopropanolSolventHCID 6228DimethylformamideSolvent

Procedure

To 20 ml of N,N-dimethylformamide were added 2.1 g of 2-t-butyl-4-chloro-5-hydroxy-3(2H)-pyridazinone, 2.5 g of 5-chloromethyl-2-(4-chlorophenoxy)-pyridine and 1.5 g of potassium carbonate, and the mixture was stirred at 80° to 90° C. for 2 hours. After cooling, the reaction mixture was poured into 50 ml of water and extracted twice with 50 ml of benzene. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent by distillation under reduced pressure to obtain 3.9 g of a crude product. The crude product was added with a mixed solvent of isopropyl ether and 2-propanol and recrystallized therefrom to give 3.3 g of 2-t-butyl-4-chloro-5-[{6-(4-chlorophenoxy)-3-pyridyl}methyloxy]-3(2H)-pyridazinone, m.p. 150.0°~154.5° C.

Workup

  1. temperatureAfter cooling
  2. extractionextracted twice with 50 ml of benzene
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationfreed of solvent by distillation under reduced pressure
  6. customto obtain 3.9 g of a crude product
  7. customrecrystallized

Sources & evidence

ORD record
ord-08710aad35034c84be4e8eb1067b0dba
Source dataset
uspto-grants-1989_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US04837217

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes