N,N-Dimethylaniline → HCID 14280609, compound

HRID 868524Notes

Reaction equation

HRID 868524 reaction equation
[F:1][C:2]([F:18])([F:17])[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][CH:11]=[CH:10][CH:9]=3.CN(C)C1C=CC=CC=1.O=P(Cl)(Cl)[Cl:30]>C(#N)C>[Cl:30][C:15]1[C:6]2[N:7]([C:3]([C:2]([F:18])([F:17])[F:1])=[N:4][N:5]=2)[C:8]2[C:13]([N:14]=1)=[CH:12][CH:11]=[CH:10][CH:9]=2

Participants

5

Reactant 3

HCID 949N,N-DimethylanilineHCID 24813Phosphorus oxychlorideHCID 178517133HCID 178517133, compound

Product 1

HCID 14280609HCID 14280609, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To a suspension of 1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxalin-4-ol (2.5 g; 0.01 mole) in 60 ml of acetonitrile, Et4N+Cl- (2.4 g) followed by N,N-dimethylaniline (1.7 ml) and POCl3 (3.75 ml) were added. Reaction mixture was refluxed for 20 hours. Volatiles were removed under reduced pressure, residue was dissolved in CHCl3 (100 ml) and added to the ice-water. Layers were separated, the aqueous layer was extracted with chloroform (2×200 ml). The combined extract was washed with 5% NaHCO3 (2×120 ml) followed by brine (2×50 ml). It was dried over MgSO4, filtered, and volatiles were removed. The residue was crystallized from chloroform-hexane affording 1.78 g of 4-chloro-1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxaline; mass spectrum m/e, 272 (m+).

Workup

  1. additionwere added
  2. customReaction mixture
  3. temperaturewas refluxed for 20 hours
  4. customVolatiles were removed under reduced pressure, residue
  5. dissolutionwas dissolved in CHCl3 (100 ml)
  6. additionadded to the ice-water
  7. customLayers were separated
  8. extractionthe aqueous layer was extracted with chloroform (2×200 ml)
  9. extractionThe combined extract
  10. washwas washed with 5% NaHCO3 (2×120 ml)
  11. dry with materialIt was dried over MgSO4
  12. filtrationfiltered
  13. customvolatiles were removed
  14. customThe residue was crystallized from chloroform-hexane affording 1.78 g of 4-chloro-1-(trifluoromethyl)[1,2,4]triazolo[4,3-a]quinoxaline

Sources & evidence

ORD record
ord-ec926e74861146a3bed16f7805ee13e0
Source dataset
uspto-grants-1988_10
Patent number
US04780464

Reaction notes

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