Water → 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole

HRID 451005

反応式

HRID 451005 の反応式
[CH3:1][C:2]1[N:6]=[CH:5][NH:4][N:3]=1.Cl[C:8]1[CH:13]=[CH:12][C:11]([N+:14]([O-:16])=[O:15])=[CH:10][C:9]=1[O:17][CH3:18].[OH-].[K+].O>CS(C)=O>[CH3:18][O:17][C:9]1[CH:10]=[C:11]([N+:14]([O-:16])=[O:15])[CH:12]=[CH:13][C:8]=1[N:4]1[CH:5]=[N:6][C:2]([CH3:1])=[N:3]1

参加物

6

反応物 4

HCID 962WaterHCID 14797Potassium HydroxideHCID 705192-Chloro-5-nitroanisoleHCID 178433329HCID 178433329、化合物

生成物 1

HCID 595777881-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole収率 26.2%

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 3-methyl-1H-1,2,4-triazole (5.0 g, 60.2 mmol), 1-chloro-2-methoxy-4-nitrobenzene (11.3 g, 60.2 mmol), and KOH flakes (3.4 g, 48.1 mmol) in anhydrous DMSO (50 mL) was heated at 80° C. for 6 h. The reaction mixture was allowed to cool to rt and was poured into 800 mL of water with vigorous stirring. The aqueous mixture was extracted with EtOAc (3×200 mL). The combined organics were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude residue was purified using silica gel chromatography (0-2% MeOH/chloroform, linear gradient) to afford 1-(2-methoxy-4-nitrophenyl)-3-methyl-1H-1,2,4-triazole (3.7 g, 26% yield). LC-MS (M+H)++235.2.

後処理

  1. temperatureto cool to rt
  2. extractionThe aqueous mixture was extracted with EtOAc (3×200 mL)
  3. washThe combined organics were washed with brine
  4. dry with materialdried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe crude residue was purified

出典と根拠

ORDレコード
ord-280fdf67a418445fac8e5bd8a14b8590
出典データセット
uspto-grants-2013_07
特許番号
US08486952B2

関連ノート

読み込み中…