Potassium Carbonate → HCID 71535015, compound

HRID 631092Notes

Reaction equation

HRID 631092 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23](=[N:25][C:26]#[N:27])[CH3:24])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1.S([O-])(O[O-])(=O)=[O:29].[K+].[K+].C(=O)([O-])[O-].[K+].[K+].S([O-])([O-])(=O)=S.[Na+].[Na+]>ClCCl.O.C(O)C.CO>[O:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[CH:3]=[C:2]1[C:10]1[N:14]2[N:15]=[C:16]([O:19][CH2:20][CH2:21][CH2:22][S:23](=[N:25][C:26]#[N:27])([CH3:24])=[O:29])[CH:17]=[CH:18][C:13]2=[N:12][CH:11]=1

Participants

9

Reactant 4

HCID 11430Potassium Carbonate2×HCID 24477Sodium Thiosulfate2×HCID 10313463Potassium peroxymonosulphate4×HCID 86729543HCID 86729543, compound

Product 1

HCID 71535015HCID 71535015, compoundYield 94%

Reagents, catalysts & solvents 4

HCID 702EthanolSolventHCID 887MethanolSolventHCID 962WaterSolvent4×HCID 6344DichloromethaneSolvent3×

Procedure

25 mL methanol were added to 1 g (2.64 mmol) [(3-{[3-(1-benzofuran-2-yl)imidazo[1,2-b]pyridazin-6-yl]oxy}propyl)(methyl)-lambda4-sulfanylidene]-cyanamide in 20 mL dichloromethane. To the clear solution 25 mL ethanol were added. 6.614 g (5.27 mmol) potassium peroxymonosulfate were dissolved in 24 mL water. 2.186 g (15.82 mmol) potassium carbonate were dissolved in 16 mL water and transferred to the potassium peroxymonosulfate solution. This solution was added in 40 min under vigorous stirring. After 19 h 200 mL dichloromethane and 50 mL of a saturated sodium thiosulfate solution was added and stirred for a few minutes. The layers were separated and the aqueous phase was extracted three times with 50 mL dichloromethane. The combined organic layers were dried over sodium sulfate, and concentrated. This residue was dissolved in 20 mL dichloromethane and 25 mL methanol. To the clear solution 25 mL ethanol were added. 6.61 g (5.27 mmol) potassium peroxymonosulfate were dissolved in 24 mL water. 2.19 g (15.85 mmol) potassium carbonate were dissolved in 16 mL water and transferred to the potassium peroxymonosulfate solution. This solution was added in 15 minutes under vigorous stirring. After 4 hours 200 mL dichloromethane and 30 mL of a saturated sodium thiosulfate solution was added and stirred for a few minutes. The layers were separated and the aqueous phase was extracted once with 50 mL dichloromethane. The combined organic layers were dried over sodium sulfate, and concentrated to yield 0.98 g (94%) of a yellow solid.

Workup

  1. additionThis solution was added in 40 min under vigorous stirring
  2. customThe layers were separated
  3. extractionthe aqueous phase was extracted three times with 50 mL dichloromethane
  4. dry with materialThe combined organic layers were dried over sodium sulfate
  5. concentrationconcentrated
  6. dissolutionThis residue was dissolved in 20 mL dichloromethane
  7. additionTo the clear solution 25 mL ethanol were added
  8. additionThis solution was added in 15 minutes under vigorous stirring
  9. stirringstirred for a few minutes
  10. customThe layers were separated
  11. extractionthe aqueous phase was extracted once with 50 mL dichloromethane
  12. dry with materialThe combined organic layers were dried over sodium sulfate
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-214d0b4151a04f0391fe39caa5452928
Source dataset
uspto-grants-2016_04
Patent number
US09320737B2

Reaction notes

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