HCID 12611939, compound → 5-Chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenone

HRID 1730760Notes

Reaction equation

HRID 1730760 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[C:12](C)=[N:13][N:14]=[C:7]1[CH:6]=[C:5]2[C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.I([O-])(=O)(=O)=[O:23].[Na+]>CC(C)=O.O.[Ru](=O)=O>[Cl:1][C:2]1[CH:11]=[CH:10][C:9]([N:8]2[CH:12]=[N:13][N:14]=[C:7]2[CH3:6])=[C:4]([CH:3]=1)[C:5]([C:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1)=[O:23]

Participants

6

Reactant 2

HCID 12611939HCID 12611939, compoundHCID 23667635Sodium periodate2×

Product 1

HCID 122460165-Chloro-2-(3-methyl-4H-1,2,4-triazol-4-yl)benzophenoneYield 23.4%

Reagents, catalysts & solvents 3

HCID 82848Ruthenium dioxideCatalystHCID 180AcetoneSolventHCID 962WaterSolvent

Procedure

A stirred suspension of 7-chloro-1-methyl-5-phenyl-s-triazolo[4,3-a]quinoline (2.94 g., 0.01 mole) in acetone (110 ml.) was cooled in an ice-bath and treated slowly with a solution prepared by adding sodium periodate (2 g.) to a stirred suspension of ruthenium dioxide (200 mg.) in water (35 ml.). The mixture became dark. Additional sodium periodate (8 g.) was added during the next 15 minutes. The ice bath was removed and the mixture was stirred for 45 minutes. Additional sodium periodate (4 g.) was added and the mixture was stirred at ambient temperature for 18 hours and filtered. The solid was washed with acetone and the combined filtrate was concentrated in vacuo. The residue was suspended in water and extracted with methylene chloride. The extract was dried over anhydrous potassium carbonate and concentrated. The residue was chromatographed on silica gel (100 g.) with 10% of methanol-90% ethyl acetate; 50 ml. fractions were collected. The product was eluted in fractions 10-20 and was crystallized from ethyl acetate to give: 0.405 g. of melting point 168°-169.5° C. and 0.291 g. of melting point 167.5°-169° (23.4% yield) of 5-chloro-2-(3-methyl-4H-1,2,4-triazol-4 -yl)benzophenone, The analytical sample had a melting point of 168° C.

Workup

  1. temperaturewas cooled in an ice-bath
  2. additiontreated slowly with a solution
  3. customprepared
  4. customThe ice bath was removed
  5. additionAdditional sodium periodate (4 g.) was added
  6. stirringthe mixture was stirred at ambient temperature for 18 hours
  7. filtrationfiltered
  8. washThe solid was washed with acetone
  9. concentrationthe combined filtrate was concentrated in vacuo
  10. extractionextracted with methylene chloride
  11. dry with materialThe extract was dried over anhydrous potassium carbonate
  12. concentrationconcentrated
  13. customThe residue was chromatographed on silica gel (100 g.) with 10% of methanol-90% ethyl acetate
  14. customfractions were collected
  15. washThe product was eluted in fractions 10-20
  16. customwas crystallized from ethyl acetate
  17. customto give

Sources & evidence

ORD record
ord-41f8641f143440e6b0bce8683569553c
Source dataset
uspto-grants-1976_11
Patent number
US03993660

Reaction notes

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