Tripropylamine → 4-Chloro-1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]-quinoxaline

HRID 1731920Notes

Reaction equation

HRID 1731920 reaction equation
[CH2:1]([C:3]1[N:7]2[C:8]3[C:13]([N:14]=[C:15](O)[C:6]2=[N:5][N:4]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][CH:9]=3)[CH3:2].P(Cl)(Cl)([Cl:21])=O.C(N(CCC)CCC)CC>>[Cl:21][C:15]1[C:6]2[N:7]([C:3]([CH2:1][CH3:2])=[N:4][N:5]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][C:11]([O:17][CH3:18])=[CH:10][CH:9]=2

Participants

4

Reactant 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 178437926HCID 178437926, compound

Product 1

HCID 133856974-Chloro-1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]-quinoxaline

Procedure

In a flame-dried reaction flask under a dry nitrogen atmosphere, there were placed 1.87 g. (0.0076 mole) of 1-ethyl-4-hydroxy-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline and 25 ml. of phosphorus oxychloride together with 1.8 ml. of tri-n-propylamine. The reaction mixture was then refluxed overnight for approximately 16 hours and finally cooled to room temperature prior to being slowly poured over ice/water. The resulting aqueous mixture was then stirred at room temperature for 30 minutes and filtered, and the solid product so obtained was subsequently washed with cold water and then dissolved in chloroform. The latter organic solution was thereafter 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 finally obtained a yellow solid product which was triturated with diethyl ether and filtered to ultimately afford 1.6 g. (80%) of pure 4-chloro-1-ethyl-7-methoxy-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 173°-175° C. Mass Spectrum: m/e, 262 (P); m/e 264 (P+2); m/e, 261 (P-1).

Workup

  1. customIn a flame-dried reaction flask under a dry nitrogen atmosphere
  2. temperatureThe reaction mixture was then refluxed overnight for approximately 16 hours
  3. filtrationfiltered
  4. customthe solid product so obtained
  5. washwas subsequently washed with cold water
  6. dissolutiondissolved in chloroform
  7. washThe latter organic solution was thereafter 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, there
  12. customwas finally obtained a yellow solid product which
  13. customwas triturated with diethyl ether
  14. filtrationfiltered to ultimately afford 1.6 g

Sources & evidence

ORD record
ord-e666a777ad814217a3f33eb5c7a51a6c
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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