Triethylamine → HCID 14280609, compound

HRID 2412921Notes

Reaction equation

HRID 2412921 reaction equation
O[C:2]1[C:3]2[N:4]([C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2.P(Cl)(Cl)([Cl:21])=O.C(N(CC)CC)C>C(Cl)(Cl)Cl>[Cl:21][C:2]1[C:3]2[N:4]([C:12]([C:15]([F:18])([F:17])[F:16])=[N:13][N:14]=2)[C:5]2[C:10]([N:11]=1)=[CH:9][CH:8]=[CH:7][CH:6]=2

Participants

5

Reactant 3

HCID 8471TriethylamineHCID 24813Phosphorus oxychlorideHCID 178517133HCID 178517133, compound

Product 1

HCID 14280609HCID 14280609, compound

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Conditions

Temperature
100 °C

Procedure

In a flame-dried reaction flask under a dry nitrogen atmosphere, there were placed 3.0 g. (0.0118 mole) of 4-hydroxy-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline and 30 ml. of phosphorous oxychloride in 2.38 g. (0.0236 mole) of triethylamine (3.3 ml.). The reaction mixture was then heated at 100° C. for a period of approximately 16 hours (i.e., overnight). Upon completion of this step, the spent mixture was cooled to room temperature, concentrated in vacuo and then partitioned between ice, water and ethanol, followed by extraction with ethyl acetate. The latter extract was next washed with saturated brine and dried over anhydrous magnesium sulfate. After removal of the drying agent by means of filtration and the solvent by means of evaporation under reduced pressure, there was obtained a residue which was subsequently dissolved in hot chloroform and filtered. The latter filtrate was then allowed to stand overnight at room temperature and filtered again. The final filtrate was then concentrated in vacuo to ultimately afford 1.4 g. of 4-chloro-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline in the form of a brownish-colored solid.

Workup

  1. customIn a flame-dried reaction flask under a dry nitrogen atmosphere
  2. temperatureUpon completion of this step, the spent mixture was cooled to room temperature
  3. concentrationconcentrated in vacuo
  4. custompartitioned between ice, water and ethanol
  5. extractionfollowed by extraction with ethyl acetate
  6. extractionThe latter extract
  7. washwas next washed with saturated brine
  8. dry with materialdried over anhydrous magnesium sulfate
  9. customAfter removal of the drying agent
  10. filtrationby means of filtration
  11. customthe solvent by means of evaporation under reduced pressure
  12. customthere was obtained a residue which
  13. filtrationfiltered
  14. filtrationfiltered again
  15. concentrationThe final filtrate was then concentrated in vacuo to ultimately afford 1.4 g

Sources & evidence

ORD record
ord-d4d0eaddf10a416fa856758722ff5a86
Source dataset
uspto-grants-1985_01
Patent number
US04495187

Reaction notes

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