HCID 20435938, compound → HCID 20435958, compound

HRID 1154038Notes

Reaction equation

HRID 1154038 reaction equation
I[CH2:2][CH2:3][C:4]1([CH3:19])[C:16](=[O:17])[N:7]2[CH2:8][CH:9]=[CH:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[N:6]2[C:5]1=[O:18].[C:20]([O-:23])(=[S:22])[CH3:21].[K+]>CC(C)=O>[C:20]([S:22][CH2:2][CH2:3][C:4]1([CH3:19])[C:16](=[O:17])[N:7]2[CH2:8][CH:9]=[CH:10][CH:11]([C:12]([O:14][CH3:15])=[O:13])[N:6]2[C:5]1=[O:18])(=[O:23])[CH3:21]

Participants

4

Reactant 2

HCID 20435938HCID 20435938, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20435958HCID 20435958, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 6.43 g (17 mmol) of methyl 2,3,5,8-tetrahydro-2-(2-iodoethyl)-2-methyl-1,3-dioxo-1H-pyrazolo-[1,2-a]pyridazine-5-carboxylate and 1.94 g (17 mmol) of potassium thioacetate in 150 ml of acetone was stirred at room temperature for 5 hours. The solvent was removed by evaporation and the residue was partitioned between dichloromethane and water. The organic phase was separated, dried over magnesium sulfate and evaporated to give methyl 2-(2-acetylthioethyl)-2,3,5,8-tetrahydro-2-methyl-1,3-dioxo-1H-pyrazolo[1,2-a]pyridazine-5-carboxylate as a mixture of diastereomers. Chromatography on silica gel using diethyl ether for the elution gave 3.81 g (69%) of diastereomer A in the form of a colorless oil and 1.26 g (23%) of diastereomer B in the form of a colorless oil.

Workup

  1. customThe solvent was removed by evaporation
  2. customthe residue was partitioned between dichloromethane and water
  3. customThe organic phase was separated
  4. dry with materialdried over magnesium sulfate
  5. customevaporated

Sources & evidence

ORD record
ord-83365bed99c5426eb7831fa2567c86a2
Source dataset
uspto-grants-1984_12
Patent number
US04487929

Reaction notes

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