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

HRID 1673190
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HRID 1673190 반응식
[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]
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8

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

생성물 1

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

시약·촉매·용매 3

HCID 1140
Toluene
용매
HCID 80711,2-Dimethoxyethane용매
HCID 21916603Acetone cyclohexane용매

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온도
80 °C

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-e3b4173cda6346a496064ade31435d05
출처 데이터셋
uspto-grants-2011_08
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07999137B2

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