Acetic Acid → HCID 21947680, compound

HRID 2214441Notes

Reaction equation

HRID 2214441 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH2:7]([N:11]1[C:19]2[C:18](=[O:20])[N:17]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[N:16]=[CH:15][C:14]=2[N:13]=[C:12]1SC)[C:8]#[C:9][CH3:10].[S:34]([O-:37])(O)=[O:35].[Na+].[C:39](O)(=O)C>O.[Cl-].[Na+]>[CH2:7]([N:11]1[C:19]2[C:18](=[O:20])[N:17]([CH2:21][C:22]3[C:31]4[C:26](=[CH:27][CH:28]=[CH:29][CH:30]=4)[CH:25]=[CH:24][CH:23]=3)[N:16]=[CH:15][C:14]=2[N:13]=[C:12]1[S:34]([CH3:39])(=[O:37])=[O:35])[C:8]#[C:9][CH3:10]

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium PermanganateHCID 21947691HCID 21947691, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 21947680HCID 21947680, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolvent2×HCID 5234Sodium ChlorideSolvent

Procedure

A solution of 500 mg of potassium permanganate in 20 ml of water was added dropwise to a solution of 600 mg (1.60 mmol) of 3-(but-2-ynyl)-2-methylsulphanyl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one in 30 ml glacial acetic acid, with stirring, at ambient temperature. After three hours at ambient temperature a sodium hydrogen sulphite solution was added dropwise until the reaction mixture was virtually decolourised again. Then it was diluted with approx. 50 ml of water and saturated with sodium chloride. The crude product precipitated was suction filtered and purified by column chromatography (aluminium oxide; eluant:dichloromethane).

Workup

  1. customThe crude product precipitated
  2. filtrationfiltered
  3. custompurified by column chromatography (aluminium oxide; eluant:dichloromethane)

Sources & evidence

ORD record
ord-7020351171024569a08e6313cddc680e
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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