N,N-Dimethylaniline → HCID 14280609, compound

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

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+).