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

HRID 1270301Notes

Reaction equation

[N+:1]([C:4]1[CH:5]=[C:6]([C:10]2[NH:15][C:14](=[O:16])[C:13]([CH:17]([NH:19][C:20](=O)[CH3:21])[CH3:18])=[N:12][N:11]=2)[CH:7]=[CH:8][CH:9]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O>ClCCCl.C(=O)([O-])O.[Na+]>[CH3:18][C:17]1[N:19]=[C:20]([CH3:21])[N:12]2[C:13]=1[C:14](=[O:16])[NH:15][C:10]([C:6]1[CH:7]=[CH:8][CH:9]=[C:4]([N+:1]([O-:3])=[O:2])[CH:5]=1)=[N:11]2

Participants

Conditions

Temperature: 95 °C

Procedure

A solution of 1.93 g (6.36 mmol) of N-{1-[3-(3-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide from example 6A in 1,2-dichloroethane is treated with 2.93 g (1.78 ml, 19.09 mmol) of phosphoryl chloride. The mixture is stirred for 3 h at 95° C. After cooling, it is hydrolyzed using a couple of drops of aqueous sodium hydrogencarbonate solution. The solvent is removed in vacuo and the residue is purified by flash chromatography (eluent gradient: dichloromethane/methanol 100:1-50:1-30:1-20:1).

Workup

temperatureAfter cooling
customThe solvent is removed in vacuo
customthe residue is purified by flash chromatography (eluent gradient: dichloromethane/methanol 100:1-50:1-30:1-20:1)

Sources & evidence

ORD record: ord-d8521838add04ee5bf143fe01701d4d0
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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