1H-1,2,4-Triazole → N-(3-nitro-5-(1H-1,2,4-triazol-1-yl)phenyl)acetamide

HRID 64139

反応式

HRID 64139 の反応式
Br[C:2]1[CH:3]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:5]=[C:6]([N+:8]([O-:10])=[O:9])[CH:7]=1.[NH:15]1[CH:19]=[N:18][CH:17]=[N:16]1.C(=O)([O-])[O-].[Cs+].[Cs+]>CN(C=O)C.[Cu-]=O>[N+:8]([C:6]1[CH:5]=[C:4]([NH:11][C:12](=[O:14])[CH3:13])[CH:3]=[C:2]([N:15]2[CH:19]=[N:18][CH:17]=[N:16]2)[CH:7]=1)([O-:10])=[O:9]

参加物

6

反応物 3

HCID 92571H-1,2,4-TriazoleHCID 10796Cesium carbonateHCID 10658908N-(3-bromo-5-nitrophenyl)acetamide

生成物 1

HCID 117777868N-(3-nitro-5-(1H-1,2,4-triazol-1-yl)phenyl)acetamide収率 86%

試薬・触媒・溶媒 2

HCID 178419072HCID 178419072、化合物触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
90 °C

実験手順

To a solution of N-(3-bromo-5-nitrophenyl)acetamide (5 g, 19.3 mmol) in DMF (50 ml) were added 1,2,4-triazole (3.3 g, 48.25 mmol, 2.5 eq.), copper(I) oxide (0.56 g, 3.86 mmol, 0.2 eq.) and cesium carbonate (12.5 g, 38.6 mmol, 2 eq.) and the mixture was heated at 90° C. for 48 h. The mixture was quenched and extracted as in Example 1(d). The solvent was distilled off and the residue was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane) to give the product in 86% yield (4.1 g). LC-MS (ESI): Calculated mass: 247.21; Observed mass: 248.0 [M+H]+ (rt: 0.257 min).

後処理

  1. customThe mixture was quenched
  2. extractionextracted as in Example 1(d)
  3. distillationThe solvent was distilled off
  4. customthe residue was purified by column chromatography (60-120 silica gel, 30% ethyl acetate in hexane)
  5. customto give the product in 86% yield (4.1 g)
  6. custom248.0 [M+H]+ (rt: 0.257 min)

出典と根拠

ORDレコード
ord-a13152e7742742738e129b0fe1ef8d0a
出典データセット
uspto-grants-2016_09
特許番号
US09447091B2

関連ノート

読み込み中…