Pyridine → HCID 178440024, compound

HRID 1507683Notes

Reaction equation

HRID 1507683 reaction equation
[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=O)[C:13]2=[C:17]([CH3:23])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]2[N:11]=1.P12(SP3(SP(SP(S3)(S1)=S)(=S)S2)=S)=[S:25].N1C=CC=CC=1>C(Cl)(Cl)Cl>[CH3:1][CH2:2][O:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[NH:15][C:14](=[S:25])[C:13]2=[C:17]([CH3:23])[N:18]=[C:19]([CH2:20][CH2:21][CH3:22])[N:12]2[N:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 14817Phosphorus sulfide (P2S5)HCID 1354069832-(2-Ethoxyphenyl)-5-methyl-7-propylimidazo[5,1-f][1,2,4]triazin-4(1H)-one

Product 1

HCID 178440024HCID 178440024, compoundYield 144.6%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

2-(2-ethoxy)-phenyl-5-methyl-7-n-propyl-3H-imidazolo[5,1-f][1,2,4]triazine-4-one (50 g (0.16 mol)), phosphorus pentasulfide (17.8 g (0.08 mol)), pyridine (250 ml) were added into a 500 ml three-neck flask with a mechanical stirrer, stirred, heated and refluxed for 6 hours, TLC tracing was performed until the reactants were totally disappeared. The solvent pyridine was removed by distilling under reduced pressure, concentrated ammonia water ((25-28%) 75 ml) and ethanol (300 ml) were added, heated and refluxed for 30 min. It was cooled, filtered, dried, and crude product (45 g) was obtained. The crude product was heated and solved into chloroform (150 ml), activated carbon (5 g) was added, stirring and reflux was performed for 30 min, it was filtered and the filtrate was washed with saturated brine and water consequently and dried with magnesium sulfate anhydrous, chloroform was removed by distilling, the obtained solid was re-crystallized with ethanol and dried, solid (38 g) was obtained with a yield of 72%.

Workup

  1. temperatureheated
  2. temperaturerefluxed for 6 hours
  3. customThe solvent pyridine was removed
  4. distillationby distilling under reduced pressure, concentrated ammonia water ((25-28%) 75 ml) and ethanol (300 ml)
  5. additionwere added
  6. temperatureheated
  7. temperaturerefluxed for 30 min
  8. temperatureIt was cooled
  9. filtrationfiltered
  10. customdried
  11. customcrude product (45 g) was obtained
  12. additionwas added
  13. stirringstirring
  14. temperaturereflux
  15. filtrationit was filtered
  16. washthe filtrate was washed with saturated brine and water consequently
  17. dry with materialdried with magnesium sulfate anhydrous, chloroform
  18. customwas removed
  19. distillationby distilling
  20. customthe obtained solid was re-crystallized with ethanol
  21. customdried

Sources & evidence

ORD record
ord-c3db390465a74511b9cabcee796ad8e8
Source dataset
uspto-grants-2015_12
Patent number
US09221825B2

Reaction notes

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