4-Nitrobenzoyl chloride → N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide

HRID 2390820ノート

反応式

HRID 2390820 の反応式
[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH2:19])[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:3])[CH3:2].[N+:22]([C:25]1[CH:33]=[CH:32][C:28]([C:29](Cl)=[O:30])=[CH:27][CH:26]=1)([O-:24])=[O:23]>C(Cl)Cl>[C:1]([C:5]1[C:6]([O:20][CH3:21])=[C:7]([NH:19][C:29](=[O:30])[C:28]2[CH:27]=[CH:26][C:25]([N+:22]([O-:24])=[O:23])=[CH:33][CH:32]=2)[CH:8]=[C:9]([C:11]2[C:12]([O:17][CH3:18])=[N:13][CH:14]=[CH:15][CH:16]=2)[CH:10]=1)([CH3:4])([CH3:2])[CH3:3]

参加物

4

反応物 2

HCID 85024-Nitrobenzoyl chlorideHCID 670698823-Tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenylamine

生成物 1

HCID 67069874N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide収率 97.3%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒2 回

反応条件

温度
0 °C

実験手順

step 3—To a solution of 100 (0.24 g, 0.85 mmol) and TEA (0.18mL, 1.3 mmol) in DCM (10 mL) at 0° C. was added 4-nitrobenzoyl chloride (0.19 g, 1.0 mmol). The resulting mixture was stirred at 0° C. for 3 h, and then warmed to RT. The mixture was then diluted with additional DCM, washed sequentially with water and brine, dried (Na2SO4), filtered and concentrated. The crude residue so obtained was purified by SiO2 chromatography eluting with EtOAc/hexane to afford 0.36 g (97%) of N-[3-tert-butyl-2-methoxy-5-(2-methoxypyridin-3-yl)phenyl]-4-nitrobenzamide (102) as a light yellow solid.

後処理

  1. temperaturewarmed to RT
  2. washwashed sequentially with water and brine
  3. dry with materialdried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue so obtained
  7. customwas purified by SiO2 chromatography
  8. washeluting with EtOAc/hexane

出典と根拠

ORDレコード
ord-f7ce140d8c5541ecb67439d7a3f681d7
出典データセット
uspto-grants-2012_09
特許番号
US08273773B2

反応ノート

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