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

HRID 57674Notes

Reaction equation

HRID 57674 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-0fab3215c10645a1a4030c0fa58d4cec
Source dataset
uspto-grants-2016_09
Patent number
US09434731B2

Reaction notes

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