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

HRID 1270300

반응식

HRID 1270300 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 111,2-Dichloroethane용매

반응 조건

온도
65 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-9024cef301194ad8a51675d7a01d73d7
출처 데이터셋
uspto-grants-2007_04
특허 번호
US07202243B2

연결된 노트

불러오는 중…