Diisopropyl Ether → 2-t-butyl-4-chloro-5{-(6-propyloxy-3-pyridyl)-methylthio}-3(2H)-pyridazinone

HRID 1904250Notes

Reaction equation

HRID 1904250 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([SH: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][CH2:23][CH2:24][CH3:25])=[N:20][CH:21]=1.C(=O)([O-])[O-].[K+].[K+].C(OC(C)C)(C)C>CN(C)C=O.O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([Cl:12])=[C:8]([S:13][CH2:15][C:16]2[CH:21]=[N:20][C:19]([O:22][CH2:23][CH2:24][CH3:25])=[CH:18][CH:17]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

7

Reactant 4

HCID 7914Diisopropyl EtherHCID 11430Potassium CarbonateHCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinoneHCID 146718235-Chloromethyl-2-propyloxypyridine

Product 1

HCID 146718242-t-butyl-4-chloro-5{-(6-propyloxy-3-pyridyl)-methylthio}-3(2H)-pyridazinoneYield 81.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

To a solution of 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 1.9 g of 5-chloromethyl-2-propyloxypyridine in 20 ml of N,N-dimethylformamide was added under stirring 1.5 g of potassium carbonate at room temperature. After additional stirring for 8 hours at room temperature, the mixture was poured into 50 ml of water and then 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 3.7 g of a crude product. The crude product was added with isopropyl ether and recrystallized therefrom to give 3.0 g of 2-t-butyl-4-chloro-5{-(6-propyloxy-3-pyridyl)-methylthio}-3(2H)-pyridazinone, m.p. 92.0°~93.5° C.

Workup

  1. extractionextracted twice with 50 ml of benzene
  2. washThe organic layer was washed with water
  3. dry with materialdried over anhydrous sodium sulfate
  4. distillationfreed of solvent by distillation under reduced pressure
  5. customto obtain 3.7 g of a crude product
  6. customrecrystallized

Sources & evidence

ORD record
ord-389f82f3d9e74ed985f037d65f5f0b0c
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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