Acetic Acid → HCID 21947647, compound

HRID 2214439Notes

Reaction equation

HRID 2214439 reaction equation
[Mn]([O-])(=O)(=O)=O.[K+].[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[N:19]=[CH:18][C:17]=2[N:16]=[C:15]1SC)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[S:37]([O-:40])(O)=[O:38].[Na+].[C:42](O)(=O)C>O>[CH2:7]([N:14]1[C:22]2[C:21](=[O:23])[N:20]([CH2:24][C:25]3[C:34]4[C:29](=[CH:30][CH:31]=[CH:32][CH:33]=4)[CH:28]=[CH:27][CH:26]=3)[N:19]=[CH:18][C:17]=2[N:16]=[C:15]1[S:37]([CH3:42])(=[O:40])=[O:38])[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 516875Potassium Permanganate2×HCID 21947667HCID 21947667, compoundHCID 23665763Sodium Bisulfite

Product 1

HCID 21947647HCID 21947647, compoundYield 55.7%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent2×

Procedure

A solution of 395 mg (2.50 mmol) of potassium permanganate was added dropwise to a solution of 700 mg (1.70 mmol) of 3-benzyl-2-methylsulphanyl-5-(naphthalen-1-ylmethyl)-3,5-dihydro-imidazo[4,5-d]pyridazin-4-one in 30 ml concentrated acetic acid with stirring at ambient temperature and stirring was continued for a further two hours. As the oxidation was not yet complete, a further 150 mg potassium permanganate, dissolved in 5 ml of water, were added and the mixture was again stirred for two hours. The reaction solution was then combined with 0.5 g sodium hydrogen sulphite, then diluted with approx. 40 ml of water and extracted three times with 20 ml of dichloromethane. The organic extracts were washed with 5% sodium hydrogen sulphite solution, then with water and dried over sodium sulphate. The crude product obtained after evaporation was purified by column chromatography (silica gel; eluant:dichloromethane with 1% ethanol).

Workup

  1. stirringstirring
  2. additionwere added
  3. stirringthe mixture was again stirred for two hours
  4. extractionextracted three times with 20 ml of dichloromethane
  5. washThe organic extracts were washed with 5% sodium hydrogen sulphite solution
  6. dry with materialwith water and dried over sodium sulphate

Sources & evidence

ORD record
ord-7b81c5c3deab460fa9f283b1439a601d
Source dataset
uspto-grants-2006_09
Patent number
US07109192B2

Reaction notes

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