Dimethyl Sulfoxide → 2-tert-butyl-4-fluoro-5-(4-tert-butylbenzyl)thio 3(2H)-pyridazinone

HRID 1751854Notes

Reaction equation

HRID 1751854 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].[F-:25].[K+].CS(C)=O>O>[C:1]([N:5]1[C:10](=[O:11])[C:9]([F:25])=[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 3

HCID 679Dimethyl SulfoxideHCID 91754PyridabenHCID 522689Potassium Fluoride

Product 1

HCID 223580622-tert-butyl-4-fluoro-5-(4-tert-butylbenzyl)thio 3(2H)-pyridazinone

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

A round bottom flask is charged with 2-tert-butyl-4-chloro-5-(4-tert-butylbenzyl)thio 3(2H)-pyridazinone (100 mg, 0.27 mmol) and to it is added potassium fluoride (23.4 mg, 0.40 mmol) and 2 ml dimethyl sulfoxide. This is heated to 120° C. for 6 hours. The reaction mixture is then poured into water and extracted with ethyl acetate. This is washed with water and dried. Purification by flash chromatography (silica gel; ethyl acetate/hexanes) gave the above mentioned compound.

Workup

  1. extractionextracted with ethyl acetate
  2. washThis is washed with water
  3. customdried
  4. customPurification by flash chromatography (silica gel; ethyl acetate/hexanes)
  5. customgave the

Sources & evidence

ORD record
ord-1ebf05d967134e29ae2bd6d47b0710b4
Source dataset
uspto-grants-2015_10
Patent number
US09161997B2

Reaction notes

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