Ethyl Acetate → 4-Chloro-5,7-dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazine

HRID 57675Notes

Reaction equation

HRID 57675 reaction equation
[CH3:1][C:2]1[N:3]=[C:4]([CH3:18])[N:5]2[C:10]=1[C:9](=O)[NH:8][C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1)=[N:6]2.C(=O)(O)[O-].[Na+].C(OCC)(=O)C.P(Cl)(Cl)([Cl:32])=O>>[Cl:32][C:9]1[C:10]2=[C:2]([CH3:1])[N:3]=[C:4]([CH3:18])[N:5]2[N:6]=[C:7]([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[N:8]=1

Participants

5

Reactant 4

HCID 8857Ethyl AcetateHCID 24813Phosphorus oxychlorideHCID 516892Sodium Bicarbonate2×HCID 1357080025,7-Dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Product 1

HCID 581700154-Chloro-5,7-dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazine

Procedure

700 mg (2.9 mmol) of 5,7-dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazin-4(3H)-one (Example 15A) were dissolved in 8 ml of phosphoryl chloride and stirred at reflux for 12 h. The reaction mixture was poured into 170 ml of saturated sodium bicarbonate solution, and solid sodium bicarbonate was added until a pH of 7 had been reached. Ethyl acetate was added, and the mixture was extracted. The organic phase was washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate and concentrated on a rotary evaporator. This gave 657 mg (80% of theory) of the product as a solid.

Workup

  1. temperatureat reflux for 12 h
  2. additionwas added until a pH of 7
  3. extractionthe mixture was extracted
  4. washThe organic phase was washed with saturated aqueous sodium chloride solution
  5. dry with materialdried over magnesium sulfate
  6. concentrationconcentrated on a rotary evaporator

Sources & evidence

ORD record
ord-eee023c61ed747e2a328f887c5641585
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

Loading…