Potassium Carbonate → HCID 12942559, compound

HRID 2198398Notes

Reaction equation

HRID 2198398 reaction equation
[Cl:1][C:2]1[N:7]=[N:6][C:5]([N:8]2[CH:12]=[N:11][C:10]([OH:13])=[N:9]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[P:20](=[S:28])(Cl)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]>C(#N)C>[P:20](=[S:28])([O:13][C:10]1[N:11]=[CH:12][N:8]([C:5]2[N:6]=[N:7][C:2]([Cl:1])=[CH:3][CH:4]=2)[N:9]=1)([O:24][CH2:25][CH3:26])[O:21][CH2:22][CH3:23]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 178518008HCID 178518008, compound

Product 1

HCID 12942559HCID 12942559, compoundYield 38.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Into a 500-ml three-necked flask equipped with a stirrer and reflux condenser were placed 6.5 g (0.033 m) of 1-(6-chloro-3-pyridazinyl)-1H-1,2,4-triazol-3-ol, 5 g (0.033 m) of potassium carbonate, 0.5 g of mercuric chloride and 100 mls of acetonitrile. The mixture was stirred and heated to 70° C. for one hour and cooled. To this mixture was added 5.6 g (0.03 m) of O,O-diethyl phosphorochloridothioate and the mixture was heated at 60° C. for 6 hours and cooled. The insolubles which formed were removed by filtration and the solvent was then removed by evaporation at 60° C. under reduced pressure. The oil which remained was taken up in 250 mls of methylene chloride sequentially washed with 200 mls of water, 200 mls of a 2 percent sodium hydroxide solution and 200 mls of water and then separated, dried over anhydrous sodium sulfate, filtered and the solvent removed by evaporation under reduced pressure leaving 4 grams of an oil product. The O,O-diethyl O-(1-(6-chloro-3-pyridazinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate product was crystallized from warm hexane in a yield of 1.7 grams (15 percent of theoretical). The product melted at 46°-49° C. NMR (60 MHz) (CDCl3, δ): 9.00 (s,1H); 8.18 (d, J=10.1 1H); 7.00 (d, J=10.0 1H); 4.35 (d of q, J=10.5, 6.5, 4H); 1.43 (t w/fine coupling, J=6.5, 6H). (Compound 5).

Workup

  1. customInto a 500-ml three-necked flask equipped with a stirrer
  2. temperaturereflux condenser
  3. temperaturecooled
  4. temperaturethe mixture was heated at 60° C. for 6 hours
  5. temperaturecooled
  6. customThe insolubles which formed
  7. customwere removed by filtration
  8. customthe solvent was then removed by evaporation at 60° C. under reduced pressure
  9. washsequentially washed with 200 mls of water, 200 mls of a 2 percent sodium hydroxide solution and 200 mls of water
  10. customseparated
  11. dry with materialdried over anhydrous sodium sulfate
  12. filtrationfiltered
  13. customthe solvent removed by evaporation under reduced pressure

Sources & evidence

ORD record
ord-42ebc1ca47ad486a8d68b1be22e6a6fb
Source dataset
uspto-grants-1982_11
Patent number
US04357327

Reaction notes

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