Potassium Carbonate → O,O-Diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate

HRID 1388782Notes

Reaction equation

HRID 1388782 reaction equation
[F:1][C:2]1[N:7]=[C:6]([N:8]2[C:12]([CH3:13])=[N:11][C:10]([OH:14])=[N:9]2)[CH:5]=[CH:4][CH:3]=1.C(=O)([O-])[O-].[K+].[K+].[P:21](=[S:29])(Cl)([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]>C(#N)C>[P:21](=[S:29])([O:14][C:10]1[N:11]=[C:12]([CH3:13])[N:8]([C:6]2[CH:5]=[CH:4][CH:3]=[C:2]([F:1])[N:7]=2)[N:9]=1)([O:25][CH2:26][CH3:27])[O:22][CH2:23][CH3:24]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 17305O,O-diethyl phosphorochloridothioateHCID 178433516HCID 178433516, compound

Product 1

HCID 12942556O,O-Diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
25 °C

Procedure

A 3-neck, 500-ml flask was charged with 9 g (0.046 m) of 1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,-4-triazol-3-ol, 6.6 grams (0.048 m) of dry potassium carbonate and 150 ml of acetonitrile. The mixture was refluxed for 2 hours and then cooled to 25° C. To this mixture was added 8.67 g (0.46 m) of O,O-diethyl phosphorochloridothioate and the mixture was heated to 75° C. for 31/2 hours. The solid material which formed was removed by filtration and the acetonitrile was removed by evaporation under reduced pressure. The solid residue which remained was taken up in ethyl ether, washed with 2 percent sodium hydroxide and dried over sodium sulfate. The desired O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate was crystallized from a 50:50 mixture of ethyl ether and hexane in a yield of 12.9 g (85 percent of theoretical). The product melted at 68°-70° C. and upon analysis was found to have carbon, hydrogen and nitrogen contents of 41.54, 4.66 and 16.05 percent, respectively, as compared to the theoretical contents of 41.62, 4.66 and 16.18 percent, respectively, as calculated for the above named compound. (Compound 2).

Workup

  1. temperatureThe mixture was refluxed for 2 hours
  2. temperaturethe mixture was heated to 75° C. for 31/2 hours
  3. customThe solid material which formed
  4. customwas removed by filtration
  5. customthe acetonitrile was removed by evaporation under reduced pressure
  6. washwashed with 2 percent sodium hydroxide
  7. dry with materialdried over sodium sulfate
  8. customThe desired O,O-diethyl O-(1-(6-fluoro-2-pyridinyl)-5-methyl-1H-1,2,4-triazol-3-yl) phosphorothioate was crystallized from a 50:50 mixture of ethyl ether and hexane in a yield of 12.9 g (85 percent of theoretical)

Sources & evidence

ORD record
ord-9b7579dbe67749ab986ee10d2b9cbaa7
Source dataset
uspto-grants-1984_02
Patent number
US04433148

Reaction notes

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