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

HRID 1270300

反応式

HRID 1270300 の反応式
[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

参加物

5

反応物 3

HCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 135738336N-{1-[3-(4-Nitrophenyl)-5-oxo-4,5-dihydro-1,2,4-triazin-6-yl]ethyl}acetamide

生成物 1

HCID 1355530695,7-Dimethyl-2-(4-nitrophenyl)imidazo[5,1-f][1,2,4]triazin-4(3H)-one

試薬・触媒・溶媒 1

HCID 111,2-Dichloroethane溶媒

反応条件

温度
65 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-9024cef301194ad8a51675d7a01d73d7
出典データセット
uspto-grants-2007_04
特許番号
US07202243B2

関連ノート

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