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Water → N'-(4'-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide

HRID 1673190
ノート
印刷プレビュー

反応式

HRID 1673190 の反応式
[C:1]([C:5]1[CH:10]=[CH:9][C:8](B(O)O)=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2].Br[C:15]1[C:20]([CH3:21])=[CH:19][C:18]([N:22]=[CH:23][N:24]([CH2:26][CH3:27])[CH3:25])=[C:17]([CH3:28])[CH:16]=1.C(=O)([O-])[O-].[Cs+].[Cs+].O>COCCOC.C1CCCCC1.CC(C)=O.C1(C)C=CC=CC=1>[C:1]([C:5]1[CH:10]=[CH:9][C:8]([C:15]2[CH:16]=[C:17]([CH3:28])[C:18]([N:22]=[CH:23][N:24]([CH2:26][CH3:27])[CH3:25])=[CH:19][C:20]=2[CH3:21])=[CH:7][CH:6]=1)([CH3:4])([CH3:3])[CH3:2]
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

8

反応物 4

HCID 962WaterHCID 10796Cesium carbonateHCID 27343204-tert-Butylphenylboronic acidHCID 59843687N'-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide

生成物 1

HCID 58214409N'-(4'-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide収率 47%

試薬・触媒・溶媒 3

HCID 1140
Toluene
溶媒
HCID 80711,2-Dimethoxyethane溶媒
HCID 21916603Acetone cyclohexane溶媒

反応条件

温度
80 °C

実験手順

The reaction is carried out using inert conditions (argon or nitrogen atmosphere, dry solvents). A suspension of 0.3 g (1.8 mmol) of (4-tert-butylphenyl)boronic acid, 0.4 g (1.5 mmol) of N′-(4-bromo-2,5-dimethylphenyl)-N-ethyl-N-methylimidoformamide, 1.5 g (4.5 mmol) caesium carbonate and 0.03 g (0.03 mmol) tetrakis(triphenylphosphin)palladium in 3.5 ml of 1,2-dimethoxyethan was stirred for 16 hrs at 80° C. At room temperature 5 ml of water and 15 ml of toluene were added. The organic layer was separated, the watery layer was again extracted using 15 ml of toluene. The combined organic layers were dried over magnesium sulfate and concentrated in vacuo. Column chromatographic (cyclohexane/aceton:4/1) yielded 0.23 g (0.7 mmol) 47% of N′-(4′-tert-butyl-2,5-dimethylbiphenyl-4-yl)-N-ethyl-N-methylimidoformamide; log P (pH 2.3)=2.67.

後処理

  1. customThe organic layer was separated
  2. extractionthe watery layer was again extracted
  3. dry with materialThe combined organic layers were dried over magnesium sulfate
  4. concentrationconcentrated in vacuo

出典と根拠

ORDレコード
ord-e3b4173cda6346a496064ade31435d05
出典データセット
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US07999137B2

反応ノート

読み込み中…

このページの内容参加物反応条件実験手順後処理出典と根拠反応ノート