Sodium Iodide → HCID 20557491, compound

HRID 1660126Notes

Reaction equation

HRID 1660126 reaction equation
Cl[CH2:2][N:3]1[C:15](=[O:16])[N:6]2[CH2:7][CH:8]=[CH:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[N:5]2[C:4]1=[O:17].[C:18]([O-:21])(=[S:20])[CH3:19].[K+].[I-].[Na+]>CC(C)=O>[C:18]([S:20][CH2:2][N:3]1[C:15](=[O:16])[N:6]2[CH2:7][CH:8]=[CH:9][CH:10]([C:11]([O:13][CH3:14])=[O:12])[N:5]2[C:4]1=[O:17])(=[O:21])[CH3:19]

Participants

5

Reactant 3

HCID 5238Sodium IodideHCID 13144517HCID 13144517, compoundHCID 23670855Potassium ethanethioate

Product 1

HCID 20557491HCID 20557491, compoundYield 59%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

3.24 g (0.0125 mol) of methyl 2-chloromethyl-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylate and 2.29 g (0.02 mol) of potassium thioacetate were refluxed together in 400 ml of acetone with a catalytic amount of sodium iodide for 19 hours. The acetone was removed by evaporation and the residue was partitioned between 250 ml of ethyl acetate and 200 ml of saturated sodium chloride solution. The organic layer was separated, dried over magnesium sulphate and evaporated to give a yellow oil. This oil was chromatographed on silica gel using chloroform/ethyl acetate (1:1) for the elution to give 2.19 g (59%) of methyl 2-acetylthiomethyl-2,3,5,8-tetrahydro-1,3-dioxo-1H-1,2,4-triazolo[1,2-a]pyridazine-5-carboxylate in the form of a colourless solid of melting point 110°-111° C. (from chloroform/hexane).

Workup

  1. customThe acetone was removed by evaporation
  2. customthe residue was partitioned between 250 ml of ethyl acetate and 200 ml of saturated sodium chloride solution
  3. customThe organic layer was separated
  4. dry with materialdried over magnesium sulphate
  5. customevaporated
  6. customto give a yellow oil
  7. customThis oil was chromatographed on silica gel
  8. washfor the elution

Sources & evidence

ORD record
ord-c92f42aa916646258a4fd4bea8ad6aec
Source dataset
uspto-grants-1981_12
Patent number
US04307094

Reaction notes

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