Hydrogen Peroxide → HCID 19598444, compound

HRID 611774Notes

Reaction equation

HRID 611774 reaction equation
[H-].[CH3:2][C:3]1[C:4]([CH2:15][S:16][C:17]2[NH:18][C:19]3[CH:25]=[CH:24][CH:23]=[CH:22][C:20]=3[N:21]=2)=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:14])([F:13])[F:12].OO.S([O-])([O-])(=[O:30])=S.[Na+].[Na+]>[V+4].C(CC(=O)C)(=O)C.C(O)C>[OH2:9].[CH3:2][C:3]1[C:4]([CH2:15][S:16]([C:17]2[NH:21][C:20]3[CH:22]=[CH:23][CH:24]=[CH:25][C:19]=3[N:18]=2)=[O:30])=[N:5][CH:6]=[CH:7][C:8]=1[O:9][CH2:10][C:11]([F:13])([F:12])[F:14]

Participants

6

Reactant 3

HCID 784Hydrogen PeroxideHCID 24477Sodium ThiosulfateHCID 69944624HCID 69944624, compound

Product 1

HCID 19598444HCID 19598444, compound

Reagents, catalysts & solvents 2

HCID 18533732HCID 18533732, compoundCatalystHCID 702EthanolSolvent

Conditions

Temperature
65 °C

Procedure

Forty mg. of acetylacetone vanadium(IV) was dissolved in 150 ml. of ethanol, followed by addition of 20.0 g. of 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)-pyridin-2-yl]methylthio]benzimidazole monohydride and further dropwise addition of 6.14 g. of 35% aqueous hydrogen peroxide solution at 20 to 25° C. The mixture was allowed to react at the same tempertaure for about 5 hours. After completion of the reaction, aqueous solution of sodium thiosulfate(2.7 g./16 ml.) was added, followed by vigorous stirring for about 10 minutes. The precipitated crystals were collected by filtration and washed with ice-cooled ethanol-water mixture (8:2). To the resultant crystals was added 90 ml. of ethanol-water mixture(9:1), and the mixture was heated to 60 to 70° C. under stirring to dissolve the crystals. The insolubles were filtered off while the mixture was hot. The filtrate was ice-cooled to precipitate crystals. The precipitated crystals were collected by filtration, washed with ice-cooled ethanol-water(8:2) and dried under reduced pressure at room temperature to give 2-[[3-methyl-4-(2,2,2-trifluoroethoxy)pyridin-2-yl]methylsulfinyl]-benzimidazole monohydrate, monoethanolate solvate as white needles. Yield:21.2 g.(91.0%).

Workup

  1. customat 20 to 25° C
  2. customto react at the same tempertaure for about 5 hours
  3. additionwas added
  4. filtrationThe precipitated crystals were collected by filtration
  5. washwashed with ice-
  6. temperaturecooled ethanol-water mixture (8:2)
  7. additionTo the resultant crystals was added 90 ml
  8. stirringunder stirring
  9. dissolutionto dissolve the crystals
  10. filtrationThe insolubles were filtered off while the mixture
  11. temperaturecooled
  12. customto precipitate crystals
  13. filtrationThe precipitated crystals were collected by filtration
  14. washwashed with ice-
  15. temperaturecooled ethanol-water(8:2)
  16. customdried under reduced pressure at room temperature

Sources & evidence

ORD record
ord-66c18b55e8c640c5831d53b3e381e92e
Source dataset
uspto-grants-1999_12
Patent number
US06002011

Reaction notes

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