Tripropylamine → HCID 13385683, compound

HRID 1731906Notes

Reaction equation

HRID 1731906 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[C:9](=[CH:10][CH:11]=1)[N:8]1[CH:12]=[N:13][N:14]=[C:7]1[C:6](O)=[N:5]2.P(Cl)(Cl)([Cl:18])=O.C(N(CCC)CCC)CC>>[Cl:18][C:6]1[C:7]2[N:8]([CH:12]=[N:13][N:14]=2)[C:9]2[C:4]([N:5]=1)=[CH:3][C:2]([F:1])=[CH:11][CH:10]=2

Participants

4

Reactant 3

HCID 7616TripropylamineHCID 24813Phosphorus oxychlorideHCID 178517314HCID 178517314, compound

Product 1

HCID 13385683HCID 13385683, compound

Procedure

In a flame-dried reaction flask under a dry nitrogen atmosphere, there were placed 8.9 g. (0.044 mole) of 7-fluoro-4-hydroxy-[1,2,4]triazolo[4,3-a]quinoxaline and 160 ml. of phosphorus oxychloride together with 8.9 ml. of tri-n-propylamine. The reaction mixture was then refluxed overnight for approximately 16 hours and finally cooled to room temperature before being poured over ice/water with mechanical stirring. 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 triturated with ethyl acetate to ultimately afford 7.0 g. (71%) of pure 4-chloro-7-fluoro-[1,2,4]triazolo[4,3-a]quinoxaline, m.p. 305°-308° C. Mass Spectrum: m/e, 222 (P); m/e 224 (P+2).

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. customtriturated with ethyl acetate to ultimately afford 7.0 g

Sources & evidence

ORD record
ord-623ddbd8743a45f8bdd35a102d5d64ce
Source dataset
uspto-grants-1986_11
Patent number
US04623725

Reaction notes

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