Phosphorus oxychloride → 5,7-Dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

HRID 444822Notes

Reaction equation

HRID 444822 reaction equation
[O:1]=[C:2]1[C:7]([CH:8]([NH:10][C:11](=O)[CH3:12])[CH3:9])=[N:6][N:5]=[C:4]([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[NH:3]1.P(Cl)(Cl)(Cl)=O>ClCCCl>[CH3:9][C:8]1[N:10]=[C:11]([CH3:12])[N:6]2[C:7]=1[C:2](=[O:1])[NH:3][C:4]([C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1)=[N:5]2

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 136024651N-[1-(5-Oxo-3-phenyl-4,5-dihydro-1,2,4-triazin-6-yl)ethyl]acetamide

Product 1

HCID 1357080025,7-Dimethyl-2-phenylimidazo[5,1-f][1,2,4]triazin-4(3H)-one

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

8.34 g (32.3 mmol) of N-[1-(5-oxo-3-phenyl-4,5-dihydro-1,2,4-triazin-6-yl)ethyl]acetamide] (Example 14A) were dissolved in 330 ml of 1,2-dichloroethane and 4.5 ml (48.5 mmol) of phosphoryl chloride were added. The mixture was stirred under reflux for 24 h. After cooling, the precipitate was filtered off and washed with water and diethyl ether. The product was subsequently dried under high vacuum. This gave 4.6 g (59% of theory) of the product as a solid.

Workup

  1. temperatureunder reflux for 24 h
  2. temperatureAfter cooling
  3. filtrationthe precipitate was filtered off
  4. washwashed with water and diethyl ether
  5. customThe product was subsequently dried under high vacuum

Sources & evidence

ORD record
ord-528d8b8559a64bb19e01fd9348c44b11
Source dataset
uspto-grants-2013_07
Patent number
US08476267B2

Reaction notes

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