3-[2-(4-Toluenesulfonyloxy)propyl]pyridazine → 3-(2-Acetylthiopropyl)pyridazine

HRID 566248Notes

Reaction equation

HRID 566248 reaction equation
C1(C)C=CC(S(O[CH:11]([CH3:19])[CH2:12][C:13]2[N:14]=[N:15][CH:16]=[CH:17][CH:18]=2)(=O)=O)=CC=1.[C:21]([O-:24])(=[S:23])[CH3:22].[K+]>CC(C)=O>[C:21]([S:23][CH:11]([CH3:19])[CH2:12][C:13]1[N:14]=[N:15][CH:16]=[CH:17][CH:18]=1)(=[O:24])[CH3:22]

Participants

4

Reactant 2

HCID 212659053-[2-(4-Toluenesulfonyloxy)propyl]pyridazineHCID 23670855Potassium ethanethioate

Product 1

HCID 154753523-(2-Acetylthiopropyl)pyridazineYield 69.5%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3-[2-(4-Toluenesulfonyloxy)propyl]pyridazine (2.53 g) was dissolved in acetone (50 ml). To the solution was added potassium thioacetate (1.48 g), and the mixture was stirred for 4.5 hours under reflux. The reaction mixture was concentrated under reduced pressure. To the concentrate was added water (30 ml), which was subjected to extraction with ethyl acetate. The extract solution was dried over anhydrous magnesium sulfate, which was concentrated under reduced pressure. The concentrate was purified by a silica gel column chromatography (developing solvent: ethyl acetate-hexane 4:1→1:0) to afford the title compound (1.18 g).

Workup

  1. temperatureunder reflux
  2. concentrationThe reaction mixture was concentrated under reduced pressure
  3. additionTo the concentrate was added water (30 ml), which
  4. extractionwas subjected to extraction with ethyl acetate
  5. dry with materialThe extract solution was dried over anhydrous magnesium sulfate, which
  6. concentrationwas concentrated under reduced pressure
  7. customThe concentrate was purified by a silica gel column chromatography (developing solvent: ethyl acetate-hexane 4:1→1:0)

Sources & evidence

ORD record
ord-63e6186cf3db43dc8f18eda38f3904f1
Source dataset
uspto-grants-2001_01
Patent number
US06174877B1

Reaction notes

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