Tetrahydrofuran → HCID 15896239, compound

HRID 1274901Notes

Reaction equation

HRID 1274901 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]1[NH:12][C:11](=[O:13])[C:10]([C:14]2[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=2)=[N:9][N:8]=1.S(Cl)(Cl)=O.O1CC[CH2:30][CH2:29]1.[O-]CC.[Na+]>O>[CH2:29]([O:13][C:11]1[N:12]=[C:7]([C:2]2[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=2)[N:8]=[N:9][C:10]=1[C:14]1[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:23])[F:21])=[CH:16][CH:15]=1)[CH3:30]

Participants

6

Reactant 4

HCID 8028TetrahydrofuranHCID 24386Thionyl ChlorideHCID 2723922Sodium ethoxideHCID 1354183873-(2-Pyridinyl)-6-[4-(trifluoromethyl)phenyl]-1,2,4-triazin-5(2H)-one

Product 1

HCID 15896239HCID 15896239, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 3-(2-pyridyl)-6-(4-trifluoromethylphenyl)-1,2,4-triazin-5-one (10.00 g, 31.4 mmol) and thionyl chloride (100 ml) was heated under reflux for two hours. The mixture was allowed to cool to room temperature, and the solvent was distilled off. To the residue were added tetrahydrofuran (100 ml) and sodium ethoxide (10.69 g, 157 mmol, 15.0 eq.), and the mixture was heated under reflux for two hours. The mixture was allowed to cool to room temperature, and water (300 ml) was added to the reaction mixture. The mixture was extracted with methylene chloride (300 ml), and washed with water (200 ml), and then washed with 5% brine (200 ml). The organic layer was dried over magnesium sulfate, filtered, and concentrated under reduced pressure to remove the solvent. The resulting solid was purified by flash silica gel column chromatography (ethyl acetate-hexane) to give the title compound (7.57 g, 70%) as pale yellow prisms.

Workup

  1. temperaturewas heated
  2. temperatureunder reflux for two hours
  3. distillationthe solvent was distilled off
  4. temperaturethe mixture was heated
  5. temperatureunder reflux for two hours
  6. temperatureto cool to room temperature
  7. extractionThe mixture was extracted with methylene chloride (300 ml)
  8. washwashed with water (200 ml)
  9. washwashed with 5% brine (200 ml)
  10. dry with materialThe organic layer was dried over magnesium sulfate
  11. filtrationfiltered
  12. concentrationconcentrated under reduced pressure
  13. customto remove the solvent
  14. customThe resulting solid was purified by flash silica gel column chromatography (ethyl acetate-hexane)

Sources & evidence

ORD record
ord-3ad9422fe42a452aa97c7a7b234b8492
Source dataset
uspto-grants-2000_12
Patent number
US06159974

Reaction notes

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