Hydrogen Peroxide → Lansoprazole

HRID 1901973Notes

Reaction equation

HRID 1901973 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>[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

6

Reactant 4

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

Product 1

HCID 3883LansoprazoleYield 287%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Vanadium(IV) acetylacetonate (40 mg) was dissolved in ethanol (150 ml), to which 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyrid-2-yl]methylthio]benzimidazole (monohydrate) (20.0 g) was added and then 35% aqueous solution of hydrogen peroxide (6.14 g) was added dropwise at 20°-25° C., and the mixture was allowed to react at 20°-25° C. for about 5 hours. After completion of the reaction, a solution of sodium thiosulfate (2.7 g/16 ml) was added to the reaction mixture and stirred vigorously for about 10 minutes. The crystals were collected by filtration and washed with an ice-cooled mixture of ethanol-water (8:2). The crystals thus obtained were treated with a mixture of ethanol-water (9:1, 90 ml), heated (60°-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 (18.1 g). (yield: 91.0%).

Workup

  1. additionwas added
  2. customto react at 20°-25° C. for about 5 hours
  3. customAfter completion of the reaction
  4. filtrationThe crystals were collected by filtration
  5. washwashed with an ice-
  6. temperaturecooled
  7. additionmixture of ethanol-water (8:2)
  8. customThe crystals thus obtained
  9. temperatureheated (60°-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-99b1efc95b2443eb890b867f5584aa6f
Source dataset
uspto-grants-1996_11
Patent number
US05578732

Reaction notes

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