Potassium Carbonate → O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate

HRID 1154847Notes

Reaction equation

HRID 1154847 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[CH:12]=[N:11][C:10]([OH:13])=[N:9]2)[CH:5]=[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:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=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 178518000HCID 178518000, compound

Product 1

HCID 12942555O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioateYield 88.3%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
70 °C

Procedure

Into a 500 milliliter (ml) flask equipped with a stirrer and a reflux condenser were placed 9 grams (g) (0.05 mole (m)) of 1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-ol, 7 g (0.05 m) of potassium carbonate, 1 g of mercuric chloride and 200 mls of acetonitrile. This mixture was stirred and heated to 70° C. for two hours and allowed to cool. To this mixture was added 9 g (0.05 m) of O,O-diethyl phosphorochloridothioate and the mixture heated to 70° C. for 16 hours and allowed to cool. The insolubles were removed by filtration and the solvent was removed from the filtrate by distillation at 60° C. under reduced pressure. The oil which remained was taken up in 300 mls of methylene chloride, washed twice with 150 ml portions of water, separated, dried over anhydrous sodium sulfate, filtered and the methylene chloride was removed by distillation leaving 14 grams (84 percent of theoretical) of the desired O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-1H-1,2,4-triazol-3-yl) phosphorothioate. The product was a white solid melting at 80°-82° C. Upon analysis, the compound was found to have carbon, hydrogen and nitrogen contents of 39.33, 4.19 and 16.73 percent, respectively, as compared with the theoretical contents of 39.76, 4.25 and 16.86 percent, respectively, calculated for the above named compound. (Compound 1).

Workup

  1. customInto a 500 milliliter (ml) flask equipped with a stirrer and a reflux condenser
  2. temperatureto cool
  3. temperaturethe mixture heated to 70° C. for 16 hours
  4. temperatureto cool
  5. customThe insolubles were removed by filtration
  6. customthe solvent was removed from the filtrate by distillation at 60° C. under reduced pressure
  7. washwashed twice with 150 ml portions of water
  8. customseparated
  9. dry with materialdried over anhydrous sodium sulfate
  10. filtrationfiltered
  11. customthe methylene chloride was removed by distillation

Sources & evidence

ORD record
ord-1cdd178bb7ee48a887c23fc2c1378d3d
Source dataset
uspto-grants-1981_11
Patent number
US04298602

Reaction notes

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