Diisopropyl Ether → HCID 13822290, compound

HRID 1904260Notes

Reaction equation

HRID 1904260 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][CH:23]([CH3:25])[CH3:24])=[N:20][CH:21]=1.[OH-].[Na+].C(OC(C)C)(C)C>C1(C)C=CC=CC=1.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.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][CH:23]([CH3:25])[CH3:24])=[CH:18][CH:17]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:2])[CH3:3]

Participants

8

Reactant 4

HCID 7914Diisopropyl EtherHCID 14798Sodium HydroxideHCID 134692424-Chloro-2-(1,1-dimethylethyl)-5-mercapto-3(2H)-pyridazinoneHCID 14671836HCID 14671836, compound

Product 1

HCID 13822290HCID 13822290, compoundYield 81.1%

Reagents, catalysts & solvents 3

HCID 74236Tetrabutylammonium BromideCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
40 °C

Procedure

To a solution of 2.2 g of 2-t-butyl-4-chloro-5-mercapto-3(2H)-pyridazinone and 2.0 g of 5-chloromethyl-2-i-propyloxypyridine in 50 ml of toluene were added 8.8 g of a 5% aqueous solution of sodium hydroxide and 0.2 g of tetra-n-butylammonium bromide, and the mixture was stirred at 40° C. for 5 hours. After termination of the reaction, water was added thereto to remove the aqueous layer. The organic layer was washed with water, dried over anhydrous sodium sulfate and then freed of solvent of distillation under reduced pressure to give 3.7 g of a crude product. The crude product was added with i-propyl ether and recrystallized therefrom to obtain 3.0 g of 2-t-butyl-4-chloro-5-{(6-i-propyloxy-3-pyridyl)-methylthio}-3(2H)-pyridazinone, m.p. 111.2°~113.3° C.

Workup

  1. additionwas added
  2. customto remove the aqueous layer
  3. washThe organic layer was washed with water
  4. dry with materialdried over anhydrous sodium sulfate
  5. distillationfreed of solvent of distillation under reduced pressure
  6. customto give 3.7 g of a crude product
  7. customrecrystallized

Sources & evidence

ORD record
ord-176cd66623364571b65246ca79e0c7e2
Source dataset
uspto-grants-1989_06
Patent number
US04837217

Reaction notes

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