Tripropylamine → HCID 20227408, compound

HRID 1731923Notes

Reaction equation

HRID 1731923 reaction equation
[F:1]C1C=C2C(N=C(O)C3N2C(C(F)(F)F)=NN=3)=CC=1.P(Cl)(Cl)(Cl)=O.C(N(CCC)CCC)CC.[Cl:35][C:36]1[C:37]2[N:38]([C:47]([C:50]([F:53])([F:52])[F:51])=[N:48][N:49]=2)[C:39]2[C:44]([N:45]=1)=[CH:43][CH:42]=[C:41](F)[CH:40]=2>>[Cl:35][C:36]1[C:37]2[N:38]([C:47]([C:50]([F:53])([F:52])[F:51])=[N:48][N:49]=2)[C:39]2[C:44]([N:45]=1)=[CH:43][C:42]([F:1])=[CH:41][CH:40]=2

Participants

5

Reactant 4

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 13385701HCID 13385701, compoundHCID 178517186HCID 178517186, compound

Product 1

HCID 20227408HCID 20227408, compound

Procedure

In a flame-dried 250 ml. three-necked reaction flask under a dry nitrogen atmosphere, there were placed 12.5 g. (0.046 mole) of 8-fluoro-4-hydroxy-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline and 85 ml. of phosphorus oxychloride together with 17.5 ml. of tri-n-propylamine. The reaction mixture was then refluxed overnight for approximately 16 hours and finally cooled to room temperature (~20° C.) prior to being slowly poured over 1000 ml. of ice/water with the aid of mechanical stirring. The resulting aqueous mixture was next stirred for an additional period of 30 minutes at room temperature, followed by extraction with three-300 ml. portions of chloroform. The combined chloroform layers were then successively washed with saturated aqueous sodium bicarbonate solution, water and saturated brine and finally 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 finally obtained a yellow solid product which consisted of 10.47 g. (79%) of pure 4-chloro-8-fluoro-1-trifluoromethyl-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 135°-138° C. Mass Spectrum: m/e, 292/290 (P+).

Workup

  1. customthree-necked reaction flask under a dry nitrogen atmosphere, there were placed
  2. temperatureThe reaction mixture was then refluxed overnight for approximately 16 hours
  3. additionto being slowly poured over 1000 ml
  4. extractionfollowed by extraction with three-300 ml
  5. washThe combined chloroform layers were then successively washed with saturated aqueous sodium bicarbonate solution, water and saturated brine
  6. dry with materialfinally dried over anhydrous magnesium sulfate
  7. customAfter removal of the drying agent
  8. filtrationby means of filtration
  9. customthe solvent by means of evaporation under reduced pressure, there
  10. customwas finally obtained a yellow solid product which

Sources & evidence

ORD record
ord-1449b1b35efd4c33b7bc001c5d730d5d
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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