Hydrogen Peroxide → HCID 15084088, compound

HRID 1534855Notes

Reaction equation

HRID 1534855 reaction equation
[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[CH2:10][S:11][C:12]1[NH:13][CH:14]=[CH:15][N:16]=1)([CH3:3])[CH3:2].OO.C(=O)([O-])[O-:24].[Na+].[Na+]>ClCCl.CO.C(O)(=O)C.[NH4+].[O-][V](=O)=O>[CH:1]([O:4][CH2:5][CH2:6][NH:7][C:8]1[CH:20]=[CH:19][CH:18]=[CH:17][C:9]=1[CH2:10][S:11]([C:12]1[NH:16][CH:15]=[CH:14][N:13]=1)=[O:24])([CH3:3])[CH3:2]

Participants

8

Reactant 3

HCID 784Hydrogen PeroxideHCID 10340Sodium CarbonateHCID 15084074HCID 15084074, compound

Product 1

HCID 15084088HCID 15084088, compoundYield 75.8%

Reagents, catalysts & solvents 4

HCID 516859Ammonium metavanadateCatalystHCID 176Acetic AcidSolventHCID 887MethanolSolventHCID 6344DichloromethaneSolvent

Procedure

1.50 g (5.2 mmol) of 2-[2-(2-isopropoxyethylamino)benzylthio]imidazole was dissolved in a mixture of 15 ml of dichloromethane, 15 ml of methanol and 1.5 ml of acetic acid. To the resulting mixture were added 2.3 ml of 35 % aqueous hydrogen peroxide and 48 mg of ammonium metavanadate under chilling with ice. Then the mixture was stirred for 2 hrs. under chilling with ice. After the reaction was completed, 5 % aqueous sodium carbonate was added to the stirred mixture. The organic portion was collected and was subjected to extraction with 20 ml of 0.2 N aqueous sodium hydroxide. To the collected aqueous portion was little by little added 60 ml of 1 N aqueous ammonium chloride. The deposited oily product was extracted with chloroform. The chloroform extractant was dried over anhydrous sodium sulfate and then chloroform was distilled off. The residue was crystallized from ether to give 1.20 g of the desired compound as a white crystalline powder. (Yield: 75.8 %)

Workup

  1. temperatureunder chilling with ice
  2. temperatureunder chilling with ice
  3. customThe organic portion was collected
  4. extractionwas subjected to extraction with 20 ml of 0.2 N aqueous sodium hydroxide
  5. extractionThe deposited oily product was extracted with chloroform
  6. dry with materialThe chloroform extractant was dried over anhydrous sodium sulfate
  7. distillationchloroform was distilled off
  8. customThe residue was crystallized from ether

Sources & evidence

ORD record
ord-172ecf2749f44acbbbdd6cec621d57a7
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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