Hydrochloric Acid → HCID 22136182, compound

HRID 2052804Notes

Reaction equation

HRID 2052804 reaction equation
Cl[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=2)[C:5]2=[N:12][N:13]=[C:14]([C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)[N:4]2[N:3]=1.[OH2:21].Cl.[OH-:23].[Na+].[CH3:25]S(C)=O>CO.[Cu]>[C:15]1([C:14]2[N:4]3[N:3]=[C:2]([C:25]([OH:23])=[O:21])[C:11]4[C:6]([C:5]3=[N:12][N:13]=2)=[CH:7][CH:8]=[CH:9][CH:10]=4)[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=1

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 679Dimethyl SulfoxideHCID 962Water2×HCID 14798Sodium HydroxideHCID 15025636-chloro-3-phenyl-[1,2,4]triazolo[3,4-a]phthalazine

Product 1

HCID 22136182HCID 22136182, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 887MethanolSolvent

Conditions

Temperature
140 °C

Procedure

A mixture of 6-Chloro-3-phenyl-1,2,4-Triazolo[3,4-a]phthalazine (2.0 g, prepared according to procedures described in Zh. Org. Khim. (1975), 11(7), 1570-2 and J. Med. Chem. (1988), 31(6), 1115-23.) and copper cynaide (2.0 g) in 50 ml of DMSO is stirred at 140° C. overnight. The mixture is cooled, poured into water and extracted with methylene chloride. The organic layer is washed with water, dried over Na2SO4 and concentrated to give a tan solid which is then dissolved in 50 mL of methanol. The resulting solution is saturated with HCl gas and the mixture is stirred at room temperature overnight. 20 mL of water and 1 mL of 10 N NaOH solution are added, the resulting mixture is then heated under reflux for 4 hours. The methanol is then evaporated in vacuo, and the remaining mixture is diluted with water. After adjusting the pH to 4-5 with 1N HCl, the solid is collected by filtration, and dried to give the title compound as a solid.

Workup

  1. temperatureThe mixture is cooled
  2. extractionextracted with methylene chloride
  3. washThe organic layer is washed with water
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto give a tan solid which
  7. stirringthe mixture is stirred at room temperature overnight
  8. temperaturethe resulting mixture is then heated
  9. temperatureunder reflux for 4 hours
  10. customThe methanol is then evaporated in vacuo
  11. additionthe remaining mixture is diluted with water
  12. filtrationthe solid is collected by filtration
  13. customdried

Sources & evidence

ORD record
ord-123e795be0194380bcf91486dc90f692
Source dataset
uspto-grants-2008_02
Patent number
US07326709B2

Reaction notes

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