Pyridaben → 2-t-butyl-4-butyl-5-(p-t-butylbenzylthio)-3(2H)-pyridazinone

HRID 2352028Notes

Reaction equation

HRID 2352028 reaction equation
[C:1]([N:5]1[C:10](=[O:11])[C:9](Cl)=[C:8]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2].[CH2:25]([Li])[CH2:26][CH2:27][CH3:28]>O1CCCC1.CCCCCC>[C:1]([N:5]1[C:10](=[O:11])[C:9]([CH2:25][CH2:26][CH2:27][CH3:28])=[C:8]([S:13][CH2:14][C:15]2[CH:20]=[CH:19][C:18]([C:21]([CH3:24])([CH3:23])[CH3:22])=[CH:17][CH:16]=2)[CH:7]=[N:6]1)([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 2

HCID 91754PyridabenHCID 178418339Butyllithium

Product 1

HCID 138251552-t-butyl-4-butyl-5-(p-t-butylbenzylthio)-3(2H)-pyridazinone

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8058HexaneSolvent

Procedure

To a solution of 0.73 g (0.002 mol) of the 2-t-butyl-5-(p-t-butylbenzylthio)-4-chloro-3(2H)-pyridazinone thus obtained dissolved in 20 ml of tetrahydrofuran was added 3.0 ml of a solution of 10% butyl lithium dissolved in hexane at -70° C. under stirring. The reaction temperature was gradually raised from -70° C. to room temperature, and then the reaction mixture was stirred at room temperature for one hour. The reaction mixture was poured into 50 ml of ice water and extracted with 50 ml of chloroform. The resulting chloroform layer was washed with 100 ml of water, dried over anhydrous sodium sulfate and freed of solvent by distillation to give 0.65 g of a crude product. The crude product was purified by preparative thin layer chromatography on silica gel (developer:benzene) to obtain 0.38 g of 2-t-butyl-4-butyl-5-(p-t-butylbenzylthio)-3(2H)-pyridazinone.

Workup

  1. temperatureThe reaction temperature was gradually raised from -70° C. to room temperature
  2. stirringthe reaction mixture was stirred at room temperature for one hour
  3. extractionextracted with 50 ml of chloroform
  4. washThe resulting chloroform layer was washed with 100 ml of water
  5. dry with materialdried over anhydrous sodium sulfate
  6. distillationfreed of solvent by distillation
  7. customto give 0.65 g of a crude product
  8. customThe crude product was purified by preparative thin layer chromatography on silica gel (developer:benzene)

Sources & evidence

ORD record
ord-894f234407ac45dd993e8c15102e137a
Source dataset
uspto-grants-1989_10
Patent number
US04874861

Reaction notes

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