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

HRID 1974126Notes

Reaction equation

HRID 1974126 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.) is 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 becomes dark. Additional sodium periodate (8 g.) is added during the next 15 minutes. The ice bath is removed and the mixture stirred for 45 minutes. Additional sodium periodate (4 g.) is added and the mixture is stirred at ambient temperature for 18 hours and filtered. The solid is washed with acetone and the combined filtrate is concentrated in vacuo. The residue is suspended in water and extracted with methylene chloride. The extract is dried over anhydrous potassium carbonate and concentrated. The residue is chromatographed on silica gel (100 g.) with a solution of 10% methanol and 90% ethyl acetate; 50 ml. fractions are collected. The product is eluted in fractions 10-20 and 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 has a melting point of 168° C.

Workup

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

Sources & evidence

ORD record
ord-f3017c76955245f68c39950ade17b422
Source dataset
uspto-grants-1976_12
Patent number
US04000153

Reaction notes

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