Ammonia → [1,2,4]Triazolo[4,3-a]quinazoline, 7-chloro-1-methyl-5-phenyl-

HRID 1414896Notes

Reaction equation

HRID 1414896 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([N:16]2[C:20](Br)=[N:19][N:18]=[C:17]2[CH3:22])=[C:6]([CH:15]=1)[C:7]([C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=1)=O.[NH3:23]>CS(C)=O.C(Cl)(Cl)Cl>[CH3:22][C:17]1[N:16]2[C:5]3[C:6]([C:7]([C:9]4[CH:14]=[CH:13][CH:12]=[CH:11][CH:10]=4)=[N:23][C:20]2=[N:19][N:18]=1)=[CH:15][C:2]([Cl:1])=[CH:3][CH:4]=3

Participants

5

Reactant 2

HCID 222AmmoniaHCID 12246017HCID 12246017, compound

Product 1

HCID 1869146[1,2,4]Triazolo[4,3-a]quinazoline, 7-chloro-1-methyl-5-phenyl-

Reagents, catalysts & solvents 2

HCID 679Dimethyl SulfoxideSolventHCID 6212ChloroformSolvent

Procedure

In the next place, a solution of 0.5 g of the above-mentioned 5-chloro-2-(3-methyl-5-bromo-4H-1,2,4-triazol-4-yl)benzophenone in 20 ml of dimethylsulfoxide was heated, with stirring, at about 180° C for 10 hours, during which ammonia gas was continuously passed into the reaction mixture. After cooling, the reaction mixture was poured into ice-water and the resulting crystals were filtered, washed with water and dried. The crystals thus obtained was dissolved in chloroform and chromatographed on silica gel using chloroform as an eluent. The product thus separated was recrystallized from isopropyl ether to give 1-methyl-5-phenyl-7-chloro-s-triazolo[4,3-a]quinazoline, m.p. 325° - 327° C.

Workup

  1. temperatureAfter cooling
  2. filtrationthe resulting crystals were filtered
  3. washwashed with water
  4. customdried
  5. customThe crystals thus obtained
  6. customchromatographed on silica gel
  7. customThe product thus separated
  8. customwas recrystallized from isopropyl ether

Sources & evidence

ORD record
ord-f8f3a259f30945d793bd79cc3c95e98d
Source dataset
uspto-grants-1977_01
Patent number
US04002755

Reaction notes

Loading…