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

HRID 1270300Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][C:7]([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:6][CH:5]=1)([O-:3])=[O:2].P(Cl)(Cl)(Cl)=O.C(=O)([O-])O.[Na+]>ClCCCl>[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:7]1[CH:8]=[CH:9][C:4]([N+:1]([O-:3])=[O:2])=[CH:5][CH:6]=1)=[N:11]2

Participants

Conditions

Temperature: 65 °C

Procedure

A solution of 13.76 g (8.13 mmol) of N-{1-[3-(4-nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide from example 5A in 150 ml of 1,2-dichloroethane is treated with 20.87 g (12.69 ml, 136.11 mmol) of phosphoryl chloride while cooling with an ice bath. The mixture is stirred for 4 h at 65° C. After cooling, it is hydrolyzed using aqueous sodium hydrogencarbonate solution. The solvent of the organic phase is removed in vacuo and the residue is purified by flash chromatography (eluent gradient:dichloromethane/methanol 200:1-100:1-50:1).

Workup

temperaturewhile cooling with an ice bath
temperatureAfter cooling
customThe solvent of the organic phase is removed in vacuo
customthe residue is purified by flash chromatography (eluent gradient:dichloromethane/methanol 200:1-100:1-50:1)

Sources & evidence

ORD record: ord-9024cef301194ad8a51675d7a01d73d7
Source dataset: uspto-grants-2007_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07202243B2

Reaction notes

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