Water → 2-(4-chloro-1H-imidazol-1-yl)-3-methoxy-5-nitropyridine

HRID 451012ノート

反応式

HRID 451012 の反応式
[Cl:1][C:2]1[N:3]=[CH:4][NH:5][CH:6]=1.Cl[C:8]1[C:13]([O:14][CH3:15])=[CH:12][C:11]([N+:16]([O-:18])=[O:17])=[CH:10][N:9]=1.[OH-].[K+].O>CS(C)=O>[Cl:1][C:2]1[N:3]=[CH:4][N:5]([C:8]2[C:13]([O:14][CH3:15])=[CH:12][C:11]([N+:16]([O-:18])=[O:17])=[CH:10][N:9]=2)[CH:6]=1

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 234561522-Chloro-3-methoxy-5-nitropyridineHCID 178478287HCID 178478287、化合物

生成物 1

HCID 580753262-(4-chloro-1H-imidazol-1-yl)-3-methoxy-5-nitropyridine収率 77.4%

試薬・触媒・溶媒 1

HCID 679Dimethyl Sulfoxide溶媒

反応条件

温度
80 °C

実験手順

A mixture of 4-chloro-1H-imidazole (2.72 g, 26.5 mmol), 2-chloro-3-methoxy-5-nitropyridine (5.0 g, 26.5 mmol), and KOH flakes 1.488 g, 26.5 mmol) in anhydrous DMSO (25 mL) was heated at 80° C. for 5 h. The reaction mixture was allowed to cool to rt and was poured into 1.0 L of water with vigorous stirring. The mixture was stirred at rt for 16 h. The precipitate was collected by vacuum filtration using a coarse sintered glass funnel The solid was dried under high vacuum for 24 h to provide 2-(4-chloro-1H-imidazol-1-yl)-3-methoxy-5-nitropyridine (5.22 g, 20.50 mmol, 77% yield) as a light brown solid. LC-MS (M+H)+=255.0. 1H NMR (500 MHz, DMSO-d6) δ ppm 8.94 (d, J=2.44 Hz, 1H) 8.51 (d, J=1.83 Hz, 1H) 8.42 (d, J=2.44 Hz, 1H) 8.02 (d, J=1.83 Hz, 1H) 4.12 (s, 3H).

後処理

  1. temperatureto cool to rt
  2. filtrationThe precipitate was collected by vacuum filtration
  3. customwas dried under high vacuum for 24 h

出典と根拠

ORDレコード
ord-8323896d30c845ab87b80c7bc7167891
出典データセット
uspto-grants-2013_07
特許番号
US08486952B2

反応ノート

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