Hydrogen Peroxide → Lansoprazole

HRID 1901971Notes

Reaction equation

HRID 1901971 reaction equation
[CH3:1][C:2]1[C:3]([CH2:14][S:15][C:16]2[NH:17][C:18]3[CH:24]=[CH:23][CH:22]=[CH:21][C:19]=3[N:20]=2)=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:13])([F:12])[F:11].OO.S([O-])([O-])(=[O:29])=S.[Na+].[Na+].C(O)C.O>C(O)C.[O-][V](=O)=O.[Na+]>[CH3:1][C:2]1[C:3]([CH2:14][S:15]([C:16]2[NH:20][C:19]3[CH:21]=[CH:22][CH:23]=[CH:24][C:18]=3[N:17]=2)=[O:29])=[N:4][CH:5]=[CH:6][C:7]=1[O:8][CH2:9][C:10]([F:12])([F:11])[F:13]

Participants

7

Reactant 4

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 1094080Lansoprazole sulfideHCID 19096565Water ethanol

Product 1

HCID 3883LansoprazoleYield 385.3%

Reagents, catalysts & solvents 2

HCID 4148882Sodium metavanadateCatalystHCID 702EthanolSolvent

Procedure

2-[[3-Methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (monohydrate) (10.0 g) was dissolved in ethanol (75 ml), to which was added a solution of sodium metavanadate (15 mg) in 35% aqueous solution of hydrogen peroxide (3.07 g), and allowed to react by stirring at 20°-25° for about 8 hours. After completion of the reaction an aqueous solution of sodium thiosulfate (1 g/5 ml) was added to the reaction mixture, which was stirred vigorously for about 10 minutes. The crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water (1:1). The crystals thus obtained were treated with a mixture of ethanol-water (9:1, 50 ml), heated (65°-70° C.) and stirred so that the crystals were dissolved, then the insoluble matters were removed by hot filtration. The filtrate was ice-cooled for crystallization, and the crystals were collected by filtration, washed with ice-cooled ethanol-water mixture (8:2) and dried in vacuo, to give white needles of 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylsulfinyl]benzimidazole (9.0 g). (yield: 90.5%).

Workup

  1. customto react
  2. additionwas added to the reaction mixture, which
  3. stirringwas stirred vigorously for about 10 minutes
  4. filtrationThe crystals were collected by filtration
  5. washwashed with an ice-
  6. temperaturecooled
  7. additionmixture of ethanol-water (1:1)
  8. customThe crystals thus obtained
  9. temperatureheated (65°-70° C.)
  10. stirringstirred so that the crystals
  11. dissolutionwere dissolved
  12. customthe insoluble matters were removed by hot filtration
  13. temperaturecooled for crystallization
  14. filtrationthe crystals were collected by filtration
  15. washwashed with ice-
  16. temperaturecooled ethanol-water mixture (8:2)
  17. customdried in vacuo

Sources & evidence

ORD record
ord-2028244a508f4df5b42799f2cd6b2879
Source dataset
uspto-grants-1996_11
Patent number
US05578732

Reaction notes

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