Sodium Carbonate → HCID 19908415, compound

HRID 1534861Notes

Reaction equation

HRID 1534861 reaction equation
[CH3:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[C:5]([CH2:6][S:7][C:8]2[NH:9][CH:10]=[CH:11][N:12]=2)=[C:4]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:3]=1.ClC1C=CC=C(C(OO)=[O:31])C=1.C(=O)([O-])[O-].[Na+].[Na+]>C(Cl)(Cl)Cl.CO>[CH3:1][C:2]1[C:14]([O:15][CH3:16])=[C:13]([CH3:17])[C:5]([CH2:6][S:7]([C:8]2[NH:12][CH:11]=[CH:10][N:9]=2)=[O:31])=[C:4]([NH:18][CH2:19][CH2:20][O:21][CH3:22])[CH:3]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 70297m-Chloroperbenzoic acidHCID 19908417HCID 19908417, compound

Product 1

HCID 19908415HCID 19908415, compoundYield 37.3%

Reagents, catalysts & solvents 2

HCID 887MethanolSolventHCID 6212ChloroformSolvent2×

Procedure

2.00 g (6.2 mmol) of 2-[4,6-dimethyl-5-methoxy-2-(2-methoxyethylamino)benzylthio]imidazole was dissolved in a mixture of 20 ml of chloroform and 2 ml of methanol. To the resulting solution was added 1.27 g of 85 % m-chloroperbenzoic acid under chilling with NaCl-ice for a period of 20 min. After the reaction was completed, chloroform and 5 % aqueous sodium carbonate were added. The organic portion was collected and washed twice with 20 ml of 0.05 N aqueous sodium hydroxide. The resulting mixture was then subject to extraction with 30 ml of 1 N aqueous sodium hydroxide. The aqueous portion was collected and washed with chloroform. To the washed solution was added 45 ml of 1 N aqueous ammonium chloride. The deposited oily product was extracted with dichloromethane. The dichloromethane portion was collected and dried over anhydrous sodium sulfate. Dichloromethane was distilled off and then the residue was crystallized from ether/hexane to give 0.78 g of the desired compound as a pale brown crystalline powder. (Yield: 37 %)

Workup

  1. customThe organic portion was collected
  2. washwashed twice with 20 ml of 0.05 N aqueous sodium hydroxide
  3. extractionThe resulting mixture was then subject to extraction with 30 ml of 1 N aqueous sodium hydroxide
  4. customThe aqueous portion was collected
  5. washwashed with chloroform
  6. additionTo the washed solution was added 45 ml of 1 N aqueous ammonium chloride
  7. extractionThe deposited oily product was extracted with dichloromethane
  8. customThe dichloromethane portion was collected
  9. dry with materialdried over anhydrous sodium sulfate
  10. distillationDichloromethane was distilled off
  11. customthe residue was crystallized from ether/hexane

Sources & evidence

ORD record
ord-4e1cb83deb8e4ee9816307be3d20d72d
Source dataset
uspto-grants-1992_02
Patent number
US05091403

Reaction notes

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